1-Benzofuran-5-carbaldehyde [C9H6O2] by Asch

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Rx-ID: 29109422 Find similar reactions

83%

With N-Bromosuccinimide; 2,2'azobis(isobutyronitrile) in chlorobenzene

T=80°C; 1 h;

Saitoh, Morihisa; Kunitomo, Jun; Kimura, Eiji; Iwashita, Hiroki; Uno, Yumiko; Onishi, Tomohiro; Uchiyama, Noriko; Kawamoto, Tomohiro; Tanaka, Toshimasa; Mol, Clifford D.; Dougan, Douglas R.; Textor, Garret P.; Snell, Gyorgy P.; Takizawa, Masayuki; Itoh, Fumio; Kori, Masakuni

Journal of Medicinal Chemistry, 2009 , vol. 52, # 20 p. 6270 - 6286 Title/Abstract Full Text View citing articles Show Details

75%

With N-Bromosuccinimide; 2,2'azobis(isobutyronitrile) in chlorobenzene

T=20 - 80°C; 1 h; Inert atmosphere; Hide Experimental Procedure

Nishikawa, Keisuke; Fukuda, Hiroshi; Abe, Masato; Nakanishi, Kazunari; Taniguchi, Tomoya; Nomura, Takashi; Yamaguchi, Chihiro; Hiradate, Syuntaro; Fujii, Yoshiharu; Okuda, Katsuhiro; Shindo, Mitsuru

Phytochemistry, 2013 , vol. 96, p. 132 - 147 Title/Abstract Full Text View citing articles Show Details

4.2.50. (Z)-3-(Benzofuran-5-yl)acrylic acid (cis-52)

NBS (0.656 g, 3.69 mmol) and AIBN (8.10 mg, 49.2 lmol) wereadded to a solution of 107 (0.364 g, 2.46 mmol) in chlorobenzene(7.3 mL) at room temperature under an argon atmosphere. Afterstirring for 1 h at 80 C, the mixture was cooled to room temperatureand diluted with EtOAc. The organic layers were washed withsaturated aqueous NaHCO3 and brine, dried (Na2SO4), filtered, andconcentrated in vacuo. The residue was purified by silica gel CC(EtOAc/hexane, 3:97) to afford benzofuran-5-carbaldehyde (108)(0.268 g, 1.84 mmol, 75percent) as a colorless oil: 1H-NMR (CDCl3,400 MHz) d: 6.82 (d, J = 2.0 Hz, 1H, furan-H), 7.54 (d, J = 8.8 Hz,1H, Ar– H), 7.65 (d, J = 2.0 Hz, 1H, furan-H), 7.79 (d, J = 8.8 Hz, 1H,Ar–H), 8.07 (s, 1H, Ar–H), 9.99 (s, 1H, –CHO); spectroscopic datawere consistent with those reported in the literature (van Otterloet al., 2005). 60%

With N-Bromosuccinimide; 2,2'azobis(isobutyronitrile) in chlorobenzene

DUTTA, Aloke K.

Patent: US2014/309427 A1, 2014 ;

T=80°C; 1 h; Hide Experimental Procedure

Location in patent: Paragraph 0074; 0075; 0076; 0077 ; Title/Abstract Full Text Show Details

Synthesis of Benzofuran-5-carbaldehyde

To a solution of 2,3-dihydrobenzofuran-5-carbaldehyde (1 g, 6.75 mmol, A) in Chlorobenzene (20 mL), NBS (1.44 g, 8.10 mmol), AIBN (22 mg, 0.13 mmol) were added and the mixture was stirred at 80° C. for 1 h. After cooling the reaction mixture to room temperature, it was washed with aqueous NaHCO3. The organic layer was separated and the aqueous layer was washed with CH2Cl2. The organic layers were combined, dried over Na2SO4 and concentrated under vacuum on a rotary evaporator. The crude product was purified via gradient column chromatography using hexanes and ethyl acetate (100:1 to 1:1) to obtain the desired aldehyde B as brown syrup (60percent) which solidifies at 0° C. [0076] 1H NMR (500 MHz, CDCl3): δ 10.07 (s, 1H), 8.15 (d, J=1.2 Hz, 1H), 7.87 (dd, J=1.5, 8.6 Hz, 1H), 7.73 (d, J=2.4 Hz, 1H), 7.62 (d, J=8.5 Hz, 1H), 6.90 (m, 1H). [0077] 13C NMR (125 MHz, CDCl3): δ 191.7, 158.2, 146.7, 132.2, 125.7, 124.6, 112.1, 107.2

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Stage #1: With diisobutylaluminium hydride in n-heptane; dichloromethane T=-20 - -15°C; 0.166667 h; Stage #2: With hydrogenchloride; water in nheptane; dichloromethane Hide Experimental Procedure

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Rx-ID: 10701378 Find similar reactions

Cole, Derek Cecil; Asselin, Magda; Boschelli, Diane Harris; Wissner, Allan; Wang, Yanong Daniel; Prashad, Amarnauth Shastrie; Dushin, Russell

Patent: US2007/287738 A1, 2007 ; Location in patent: Page/Page column 25 ; Title/Abstract Full Text Show Details

20:

EXAMPLE 20 Preparation of 1-benzofuran-5-carbaldehyde To a solution of 1-benzofuran-5-carbonitrile (5.0 g, 34.9 mmol) in CH2Cl2 under nitrogen at -15 to -20° C. was added DIBAL-H (41.9 mL, 41.9 mmol, 1 M/heptane) and the temperature was maintained below -15° C. After addition was complete, the reaction mixture was stirred at -15 to -20° C. for an additional 10 min. The reaction mixture was quenched via dropwise addition of aqueous 2N HCl. The organic layer was separated and washed with water, dried over sodium sulfate, and concentrated to give 4.0 g (78percent) of 1-benzofuran-5-carbaldehyde as a yellow oil. 78%

Stage #1: With diisobutylaluminium hydride in n-heptane; dichloromethane T=-20 - -15°C; 0.166667 h; Stage #2: With hydrogenchloride; water in nheptane; dichloromethane T=20°C; Hide Experimental Procedure

WYETH

Patent: WO2009/76571 A1, 2009 ; Location in patent: Page/Page column 41 ; Title/Abstract Full Text Show Details

15.a: EXAMPLE 15:PREPARATION OF 5-(5-FORMYL-I -BENZOFURAN-2-YL)-6-METHYL-4-[(4- METHYL-1 H-INDOL-5-YL)AMINO]NICOTINONITRILEStep a): Preparation of 5-formylbenzofuran.To a -150C to -2O0C solution of 1benzofuran-5-carbonitrile (5 g, 34.9 mmol) in 50 mL of dichloromethane under nitrogen was added DIBAL-H (41.9 mL, 41.9 mmol, 1.0M in heptane) such that the temperature was less than or equal to -150C. The reaction mixture was stirred for an additional 10 min at -150C to -2O0C and quenched by adding 2.0 N HCI dropwise such that the temperature was less than or equal to room temperature. The organic layer was then separated, washed with water, dried over sodium sulfate and concentrated to give 4 g (78percent) of the title compound as a yellow oil, which was used in the next step without further purification. With diisobutylaluminium hydride in dichloromethane

T=-15°C; 0.166667 h;

Prashad, Amar S.; Wang, Daniel; Subrath, Joan; Wu, Biqi; Lin, Melissa; Zhang, Mei-Yi; Kagan, Natasha; Lee, Julie; Yang, Xiaoke; Brennan, Agnes; Chaudhary, Divya; Xu, Xin; Leung, Louis; Wang, Jack; Boschelli, Diane H.

Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 19 p. 5799 - 5802 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 4607496 Find similar reactions

70%

With tert.-butyl lithium in diethyl ether; pentane

T=-78 - 8°C; 0.833333 h; Hide Experimental Procedure

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SCHERING CORPORATION; PHARMACOPEIA, INC.

Patent: WO2004/11418 A1, 2004 ; Location in patent: Page 161 ; Title/Abstract Full Text Show Details

1031:Preparative Example 1031

A solution of 5-bromobenzofuran (950 mg, 4.82 [MMOL)] in anhydrous ether (12 mL) was cooled to-78 [°C.] 1.7 M [TELT-BULI] solution in pentane (6 [ML,] 10.2 [MMOL)] was added dropwise under argon. After addition, the mixture was stirred at-78 °C for 20 min, followed by addition of a mixture of DMF (0.8 mL) and ether (1 mL). The mixture was allowed to warm to rt and stirred for 0.5 h. Ethyl acetate was added. The mixture was poured to saturated ammonium chloride solution. The organic layer was separated and concentrated. The residue was purified by column chromatography (ethyl acetate-hexanes, 1: 5 [V/V)] to give the title compound as a pale yellow solid (490 mg, [70percent).] 70%

Stage #1: 5-Bromobenzo(b)-furan With tert.butyl lithium in diethyl ether; pentane

T=-78°C; 0.333333 h; Stage #2: DMFA in diethyl ether; pentane

T=-78 - 20°C; 0.5 h; Product distribution / selectivity; Hide Experimental Procedure

SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.

Patent: WO2005/68460 A1, 2005 ; Location in patent: Page/Page column 318 ; Title/Abstract Full Text Show Details

1031:

A solution of 5-bromobenzofuran (950 mg, 4.82 mmol) in anhydrous ether (12 mL) was cooled to-78 °C. 1.7 M tert-BuLi solution in pentane (6 ml, 10.2 mmol) was added dropwise under argon. After addition, the mixture was stirred at-78 °C for 20 min, followed by addition of a mixture of DMF (0.8 mL) and ether (1 mL). The mixture was allowed to warm to rt and stirred for 0.5 h. Ethyl acetate was added. The mixture was poured to saturated ammonium chloride solution. The organic layer was separated and concentrated. The residue was purified by column chromatography (ethyl acetate-hexanes, 1: 5 v/v) to give the title compound as a pale yellow solid (490 mg, 70percent). 67%

With ammonium chloride; tert.-butyl lithium in benzene

T=-25 - 20°C; 3 h; Hide Experimental Procedure

Schering Corporation

Patent: US2004/106794 A1, 2004 ; Location in patent: Page 123 ; Title/Abstract Full Text Show Details

34.4:Preparative example34.4

To a solution of the product from Step B (2 g) in ether (20 ml) at -78 C. was added t-BuLi dropwise. After stirring for 20 min, DMF (950 mg) was added dropwise and the mixture was stirred at ?25 C. for 3 hrs and then warmed to room temperature overnight. Saturated ammonium chloride was added and the solution was extracted with ether. The ether layer was washed with brine, dried with MgSO4, filtered and concentrated in vacuo to give 980 mg of crude product (67percent).

67%

Stage #1: 5-Bromobenzo(b)-furan With tert.butyl lithium in diethyl ether

T=-78°C; 0.333333 h; Stage #2: DMFA in diethyl ether

T=-25 - 20°C; Hide Experimental Procedure

SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.

Patent: WO2005/66147 A1, 2005 ; Location in patent: Page/Page column 209 ; Title/Abstract Full Text Show Details

34.4.C:

Step C; To a solution of the product from Step B (2g) in ether (20mut) at-78°C was added t-BuLi dropwise. After stirring for 20min, DMF (950mg) was added dropwise and the mixture was stirred at-25°C for 3hrs and then warmed to room temperature overnight. Saturated ammonium chloride was added and the solution was extracted with ether. The ether layer was washed with brine, dried with MgS04, filtered and concentrated in vacuo to give 980mg of crude product (67percent). 67%

Stage #1: 5-Bromobenzo(b)-furan With tert.butyl lithium in diethyl ether

SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.

Patent: WO2005/68460 A1, 2005 ;

T=-78°C; 0.333333 h; Stage #2: DMFA in diethyl ether

T=-25 - 20°C; Product distribution / selectivity; Hide Experimental Procedure

Location in patent: Page/Page column 203 ; Title/Abstract Full Text Show Details

34.4.C:

To a solution of the product from Step B (2g) in ether (20ml) at-78°C was added t-BuLi dropwise. After stirring for 20min, DMF (950mg) was added dropwise and the mixture was stirred at-25°C for 3hrs and then warmed to room temperature overnight. Saturated ammonium chloride was added and the solution was extracted with ether. The ether layer was washed with brine, dried with MgS04, filtered and concentrated in vacuo to give 980mg of crude product (67percent). 54%

Stage #1: 5-Bromobenzo(b)-furan With iodine; magnesium in tetrahydrofuran

2.5 h; Heating / reflux; Stage #2: DMFA in tetrahydrofuran

T=-40 - 20°C; 12 h; Hide Experimental Procedure

APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.

Patent: WO2004/7491 A1, 2004 ; Location in patent: Page 52 ; Title/Abstract Full Text Show Details

1.IV:Step IV: [5-FOLMYL-L-BENZOFURAN] (Pla in scheme 2 for example [9) :] A mixture [OF 5-BROMO-1-BENZOFURAN (0. 5G),] Mg (0.92g, 0. [038MOL), I2] (1 crystal) in dry THF (2. [5ML)] under N2 atmosphere was refluxed for 30min. To this was added a solution of 5- [BROMO-1-BENZOFURAN] (4. [5G)] in 25mL of dry THF) as soon as [THE I2 COLOR] disappear and refluxed for another 2h. The reaction mixture was then cooled to-40°C and added dry DMF (3.6g) drop-wise and slowly warmed to RT for a period of 12h. The reaction mixture was then cooled to 0°C and acidified with 3N HCl to pH=2 and stirred for 30min. The reaction mixture was then diluted with water [(500ML),] extracted with ethylacetate [(2X200ML),] washed with brine and dried. The solvent was removed under vacuum and purified by column chromatography over silica gel (pet. [ETHER/CH2CL2)] to give 5-formyl-1- [BENZOFURAN] (2g, 54percent) as a liquid. LC-MS: M/Z ESI: 1.47 min, [14734 (M+1).] With tert.-butyl lithium

1.) Et2O, -78 deg C, 2.) Et2O; Multistep reaction;

Tasker, Andrew S.; Sorensen, Bryan K.; Jae, Hwan-Soo; Winn, Martin; Von Geldern, Thomas W.; Dixon, Douglas B.; Chiou, William J.; Dayton, Brian D.; Calzadila, Samuel; Hernandez, Lisa; Marsh, Kennan C.; WuWong, J. Ruth; Opgenorth, Terry J.

Journal of Medicinal Chemistry, 1997 , vol. 40, # 3 p. 322 - 330 Title/Abstract Full Text View citing articles Show Details

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With Grubb's 2nd generation catalyst in toluene

T=90°C; 3 h;

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Rx-ID: 9907261 Find similar reactions

Van Otterlo, Willem A.L.; Morgans, Garreth L.; Madeley, Lee G.; Kuzvidza, Samuel; Moleele, Simon S.; Thornton, Natalie; De Koning, Charles B.

Tetrahedron, 2005 , vol. 61, # 32 p. 7746 - 7755 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 12959016 Find similar reactions

Van Otterlo, Willem A.L.; Morgans, Garreth L.; Madeley, Lee G.; Kuzvidza, Samuel; Moleele, Simon S.; Thornton, Natalie; De Koning, Charles B.

Tetrahedron, 2005 , vol. 61, # 32 p. 7746 - 7755

2: 82 percent / [RuClH(CO)(PPh3)3] / CH2Cl2 / 14 h / 65 °C 3: 50 percent / ((Mes)2C3H5N2)Cl2Ru=CHPh / toluene / 3 h / 90 °C View Scheme

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Rx-ID: 12959487 Find similar reactions

Van Otterlo, Willem A.L.; Morgans, Garreth L.; Madeley, Lee G.; Kuzvidza, Samuel; Moleele, Simon S.; Thornton, Natalie; De Koning, Charles B.

Tetrahedron, 2005 , vol. 61, # 32 p. 7746 - 7755 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 12961917 Find similar reactions

Van Otterlo, Willem A.L.; Morgans, Garreth L.; Madeley, Lee G.; Kuzvidza, Samuel; Moleele, Simon S.; Thornton, Natalie; De Koning, Charles B.

Tetrahedron, 2005 , vol. 61, # 32 p. 7746 - 7755 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 5 steps 1: K2CO3 / acetone 2: 41 percent / 0.17 h / 250 °C / microwave irradiation 3: 89 percent / K2CO3 / acetone / 2 h / 60 °C 4: 82 percent / [RuClH(CO)(PPh3)3] / CH2Cl2 / 14 h / 65 °C 5: 50 percent / ((Mes)2C3H5N2)Cl2Ru=CHPh / toluene / 3 h / 90 °C View Scheme

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Rx-ID: 12965224 Find similar reactions

Van Otterlo, Willem A.L.; Morgans, Garreth L.; Madeley, Lee G.; Kuzvidza, Samuel; Moleele, Simon S.; Thornton, Natalie; De Koning, Charles B.

Tetrahedron, 2005 , vol. 61, # 32 p. 7746 - 7755 Title/Abstract Full Text View citing articles Show Details

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1.5 h; Heating;

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Rx-ID: 9904712 Find similar reactions

Janssen, C. G. M.; Verreet, B.; Lenoir, H. A. C.; Thijssen, J. B. A.

Journal of Labelled Compounds and Radiopharmaceuticals, 2004 , vol. 47, # 4 p. 274 - 277 Title/Abstract Full Text Show Details

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Stage #1: 5-Bromobenzo(b)-furan With tert.butyl lithium in diethyl ether

T=-78°C; 0.333333 h; Stage #2: DMFA in diethyl ether

T=-25 - 20°C; 3 h; Hide Experimental Procedure

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Rx-ID: 22957089 Find similar reactions

PHARMACOPEIA, INC.

Patent: WO2004/33440 A1, 2004 ; Location in patent: Page 239-240; 348 ; Title/Abstract Full Text Show Details

34.4.C; 1031:STEP C

To a solution of the product from Step B (2g) in ether (20MI) AT-78°C was added t-BuLi dropwise. After stirring for 20min, DMF (950mg) was added dropwise and the mixture was stirred AT-25°C for 3hrs and then warmed to room temperature overnight. Saturated ammonium chloride was added and the solution was extracted with ether. The ether layer was washed with brine, dried with MGS04, filtered and concentrated in vacuo to give 980mg of crude product (67percent); A solution of 5-bromobenzofuran (950 mg, 4.82 MMOL) in anhydrous ether (12 mL) was cooled to-78 °C. 1.7 M TERT-BULI solution in pentane (6 mi, 10.2 MMOL) was added dropwise under argon. After addition, the mixture was stirred at-78 °C for 20 min, followed by addition of a mixture of DMF (0.8 mL) and ether (1 mL). The mixture was allowed to warm to rt and stirred for 0.5 h. Ethyl acetate was added. The mixture was poured to saturated ammonium chloride solution. The organic layer was separated and concentrated. The residue was purified by column chromatography (ethyl acetate-hexanes, 1: 5 V/V) to give the title compound as a pale yellow solid (490 mg, 70percent). 67%

Stage #1: 5-Bromobenzo(b)-furan With tert.butyl lithium in diethyl ether

Schering Corporation and Pharmacopeia, Inc.

Patent: US2004/147559 A1, 2004 ;

T=-78°C; 0.333333 h; Stage #2: DMFA in diethyl ether

T=-25 - 20°C; Hide Experimental Procedure

Location in patent: Page 122 ; Title/Abstract Full Text Show Details

34.4.C:Step C

To a solution ol the product from Step B (2 g) in ether (20 ml) at -78 C. was added t-BuLi dropwise. Alter stirring lor 20 min, DMF (950 mg) was added dropwise and the mixture was stirred at -25 C. lor 3 hrs and then warmed to room temperature overnight. Saturated ammonium chloride was added and the solution was extracted with ether. The ether layer was washed with brine, dried with MgSO4, filtered and concentrated in vacuo to give 980 mg ol crude product (67percent).

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Rx-ID: 17415334 Find similar reactions

Journal of Medicinal Chemistry, 1997 , vol. 40, # 3 p. 322 - 330 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 2 steps 1: polyphosphoric acid / benzene / Heating 2: 1.) t-BuLi / 1.) Et2O, -78 deg C, 2.) Et2O View Scheme

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Rx-ID: 17426326 Find similar reactions

Journal of Medicinal Chemistry, 1997 , vol. 40, # 3 p. 322 - 330 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 4096024

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With N,N,N',N',N'',N''-hexamethylphosphoric triamide; lithium chloride

T=130°C; 1.5 h;

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Hiroya, Kou; Hashimura, Kazuya; Ogasawara, Kunio

Heterocycles, 1994 , vol. 38, # 11 p. 2463 - 2472 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 4 steps 1: 85 percent / ethyldiisopropylamine / CH2Cl2 / 0.67 h / -78 - 20 °C 2: 88 percent / Pd(PPh3)2Cl2, Et3N / dimethylformamide / 1.5 h / 90 °C 3: 68 percent / K2CO3 / methanol / 8.5 h / Ambient temperature 4: 58 percent / LiCl, HMPA / 1.5 h / 130 °C View Scheme

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Rx-ID: 18049027 Find similar reactions

Hiroya, Kou; Hashimura, Kazuya; Ogasawara, Kunio

Heterocycles, 1994 , vol. 38, # 11 p. 2463 - 2472 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar Multi-step reaction with 2 steps 1: 68 percent / K2CO3 / methanol / 8.5 h / Ambient temperature 2: 58 percent / LiCl, HMPA / 1.5 h / 130 °C View Scheme

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Rx-ID: 18072454 Find similar reactions

Hiroya, Kou; Hashimura, Kazuya; Ogasawara, Kunio

Heterocycles, 1994 , vol. 38, # 11 p. 2463 - 2472 Title/Abstract Full Text View citing articles Show Details

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Multi-step reaction with 3 steps 1: 88 percent / Pd(PPh3)2Cl2, Et3N / dimethylformamide / 1.5 h / 90 °C 2: 68 percent / K2CO3 / methanol / 8.5 h / Ambient temperature 3: 58 percent / LiCl, HMPA / 1.5 h / 130 °C View Scheme

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Rx-ID: 18076640 Find similar reactions

Hiroya, Kou; Hashimura, Kazuya; Ogasawara, Kunio

Heterocycles, 1994 , vol. 38, # 11 p. 2463 - 2472 Title/Abstract Full Text View citing articles Show Details

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With hydrogenchloride; iodine; magnesium in tetrahydrofuran; ethyl acetate; N,N-dimethylformamide

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Rx-ID: 24438212 Find similar reactions

Merck and Co., Inc.

Patent: US5229381 A1, 1993 ; Title/Abstract Full Text Show Details

31.C:Step C

Step C Preparation of 5-formylbenzofuran A slurry of powdered magnesium (11.44 g) and iodine (0.12 g) in THF (120 mL) was heated to 50° C. under a N2 blanket for 0.5 hr. A 30 mL portion of the material prepared above in Example 31, Step B (90 g) in THF (225 mL) was then added at 50° C., without stirring. This mixture was aged for 0.5 hr and the the remaining 195 mL of the THF solution was added over 1.5 hr (with stirring) while maintaining a gentle reflux. When the addition was complete, the mixture was aged at 50° C. for 1 hr and then was cooled to 5° C. before DMF (45 mL) was added dropwise over 30 min while maintaining the reaction temperature between 5°-10° C. The mixture was then aged at 10° C. for 1 hr and then cooled to 5° C. before a mixture of 3N HCl (300 mL) and a 50percent sat. solution of brine (225 mL) was added while maintaining the reaction temperature below 15° C. The pH was also monitored and when the pH of the aqueous layer had fallen to 6, EtOAc (200 mL) was added and the remaining 3N HCl/brine mixture was added (final pH approx. 1.2). This mixture was stirred for 1 hr and the aqueous layer was removed and extracted with EtOAc (150 mL). The combined organic layers were washed successively with 2N HCl (100 mL) and brine (3*80 mL), dried over Na2 SO4, filtered and evaporated to dryness to give 63.6 g of the title compound as an orange oil that was of sufficient purity for use in the next step.

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ICI AUSTRALIA LIMITED

Patent: EP125059 B1, 1991 ; Title/Abstract Full Text Show Details

1.d:Example 1

d) Benzo[b]furan-5-carboxaldehyde was prepared from 5-bromobenzo[b]furan (prepared from 4-bromophenol and bromoacetaldehyde diethyl acetal by the general method described in J. Chem. Soc. Perkin 1, 1972, 556) following essentially the same procedure as that described in b) above. Benzo[b]furan-5-carboxaldehyde was obtained as an oil. Pmr spectrum (CDCl3; δ in ppm): 6.90 (1H,d); 7.55-7.93 (3H,m); 8.15 (1H,d); 10.08 (1H,s).

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Rx-ID: 25040532 Find similar reactions

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ICI Australia Limited

Patent: US4664693 A1, 1987 ; Title/Abstract Full Text Show Details

1.d:EXAMPLE 1 (d) benzo[b]furan-5-carboxaldehyde was prepared from 5-bromobenzo[b]furan (prepared from 4-bromophenol and bromoacetaldehyde diethyl acetal by the general method described in J. Chem. Soc. Perkin 1, 1972, 556) following essentially the same procedure as that described in (b) above. Benzo[b]furan-5-carboxaldehyde was obtained as an oil. Pmr spectrum (CDCl3; δ in ppm): 6.90 (1H, d); 7.55-7.93 (3H, m); 8.15 (1H, d); 10.08 (1H, s).