Reaxys
PubChem
eMolecules
Reactions (20)
Yield
Substances (5)
Citations (22)
Conditions
References
1
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Rx-ID: 393730 Find similar reactions
With hydrogenchloride; copper(l) chloride
T=70°C;
Keneford et al.
Journal of the Chemical Society, 1948 , p. 358,359 Journal of the Chemical Society, 1950 , p. 1110,1111 Full Text Show Details
Zenitz; Hartung
Journal of Organic Chemistry, 1946 , vol. 11, p. 444,447 Full Text Show Details
With Cu2Cl2; hydrogenchloride; sodium nitrite
Nelson,K.L. et al.
Journal of the American Chemical Society, 1964 , vol. 86, p. 684 - 687 Full Text View citing articles Show Details
With hydrogenchloride; copper(l) chloride; sodium nitrite
2.) 0 deg C; Yield given. Multistep reaction;
Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro
Journal of Organic Chemistry, 1994 , vol. 59, # 14 p. 3830 - 3837 Title/Abstract Full Text View citing articles Show Details
2
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Rx-ID: 1094468 Find similar reactions
With chromic acid
Montgomery,F.C.; Saunders,W.H.
Journal of Organic Chemistry, 1976 , vol. 41, p. 2368 - 2372 Full Text View citing articles Show Details
With sodium dichromate; sulfuric acid in dimethyl sulfoxide
Chang, Lu; Kuang, Yulong; Qin, Bo; Zhou, Xin; Liu, Xiaohua; Lin, Lili; Feng, Xiaoming
Organic Letters, 2010 , vol. 12, # 10 p. 2214 - 2217 Title/Abstract Full Text View citing articles Show Details
3
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Rx-ID: 4976492 Find similar reactions
76%
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With bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran
1 h; Ambient temperature;
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Tokuyama, Hidetoshi; Yokoshima, Satoshi; Yamashita, Tohru; Fukuyama, Tohru
Tetrahedron Letters, 1998 , vol. 39, # 20 p. 3189 - 3192 Title/Abstract Full Text View citing articles Show Details
4
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Rx-ID: 7247904 Find similar reactions
Warner et al.
Journal of the Chemical Society, 1962 , p. 1232 Full Text Show Details
Granito; Schultz
Journal of Organic Chemistry, 1963 , vol. 28, p. 879 Full Text View citing articles Show Details
Quellette; Levin
Journal of the American Chemical Society, 1971 , vol. 93, p. 471,472-476 Full Text Show Details
Patent: DE2059618 ; Chem.Abstr., 1972 , vol. 76, # 3551k Full Text Show Details
Wellcome
Patent: DE2064934 , 1970 ; Chem.Abstr., 1972 , vol. 76, # 33965 Full Text Show Details
5
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Musso, David L.; Mehta, Nariman B.; Soroko, Francis E.
Bioorganic and Medicinal Chemistry Letters, 1997 , vol. 7, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details
in ethanol
6
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Rx-ID: 9652583 Find similar reactions
7
Rx-ID: 7247905 Find similar reactions
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83%
With bromine; N,N-dimethyl-formamide; zinc; palladium on activated charcoal in tetrahydrofuran; toluene
T=20°C; Fukuyama coupling reaction; 48 h;
Mori, Yoshikazu; Seki, Masahiko
Tetrahedron Letters, 2004 , vol. 45, # 39 p. 7343 - 7345 Title/Abstract Full Text View citing articles Show Details
83%
With bromine; N,N-dimethyl-formamide; zinc; palladium on activated charcoal in tetrahydrofuran; toluene
T=20°C; Fukuyama coupling reaction; 48 h;
Mori, Yoshikazu; Seki, Masahiko
Advanced Synthesis and Catalysis, 2007 , vol. 349, # 11-12 p. 2027 - 2038 Title/Abstract Full Text View citing articles Show Details
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8
With aluminium trichloride; bis(trichloromethyl) carbonate in chloroform
T=50°C;
Su, Weike; Jin, Can
Organic Letters, 2007 , vol. 9, # 6 p. 993 - 996 Title/Abstract Full Text View citing articles Show Details
Multi-step reaction with 3 steps 1: NO2/HNO3 / CS2
2: H2 / Pd-C / ethanol 3: NaNO2, Cu2Cl2, HCl View Scheme
Nelson,K.L. et al.
Journal of the American Chemical Society, 1964 , vol. 86, p. 684 - 687 Full Text View citing articles Show Details
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Multi-step reaction with 2 steps 1: 1.) SOCl2, 2.) NH4OH, 3.) SOCl2 / 2.) dioxane, 3.) reflux 2: ethanol View Scheme
Rx-ID: 17455515 Find similar reactions
Musso, David L.; Mehta, Nariman B.; Soroko, Francis E.
Bioorganic and Medicinal Chemistry Letters, 1997 , vol. 7, # 1 p. 1 - 6 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 10536717 Find similar reactions
66%
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9
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Multi-step reaction with 2 steps 1: SnCl2, 7.5 N aq. HCl / acetic acid 2: 1.) NaNO2, aq. HCl, 2.) CuCl, aq. HCl / 2.) 0 deg C
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Rx-ID: 18429196 Find similar reactions
Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro
Journal of Organic Chemistry, 1994 , vol. 59, # 14 p. 3830 - 3837 Title/Abstract Full Text View citing articles Show Details
View Scheme
Multi-step reaction with 2 steps 1: H2 / Pd-C / ethanol 2: NaNO2, Cu2Cl2, HCl View Scheme
Nelson,K.L. et al.
Journal of the American Chemical Society, 1964 , vol. 86, p. 684 - 687 Full Text View citing articles Show Details
10
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Multi-step reaction with 3 steps 1: HNO3 (d=1.5) / acetic acid / -10 - 0 °C 2: SnCl2, 7.5 N aq. HCl / acetic acid 3: 1.) NaNO2, aq. HCl, 2.) CuCl, aq. HCl / 2.) 0 deg C View Scheme
Rx-ID: 18442155 Find similar reactions
Marques, Carlos Alberto; Selva, Maurizio; Tundo, Pietro
Journal of Organic Chemistry, 1994 , vol. 59, # 14 p. 3830 - 3837 Title/Abstract Full Text View citing articles Show Details
11
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12
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Rx-ID: 22495080 Find similar reactions
Multi-step reaction with 2 steps 2: H2CrO4
View Scheme
Montgomery,F.C.; Saunders,W.H.
Journal of Organic Chemistry, 1976 , vol. 41, p. 2368 - 2372 Full Text View citing articles Show Details
Multi-step reaction with 2 steps 1: tetrahydrofuran / 3.25 h / 5 - 20 °C 2: sodium t-butanolate; phen / toluene / 3 h / 80 °C / |Inert atmosphere View Scheme
Zheng, Hong-Xing; Xiao, Zu-Feng; Yao, Chuan-Zhi; Li, Qiang-Qiang; Ning, Xiao-Shan; Kang, YanBiao; Tang, Yong
Organic Letters, 2015 , vol. 17, # 24 p. 6102 - 6105 Title/Abstract Full Text View citing articles Show Details
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Rx-ID: 25047913 Find similar reactions
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With hydrogenchloride; iodine; magnesium in diethyl ether; water
Hide Experimental Procedure
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Synthelabo
Patent: US4690931 A1, 1987 ; Title/Abstract Full Text Show Details
4:2-Bromo-3'-chloropropiophenone
EXAMPLE 4 2-Bromo-3'-chloropropiophenone 4.86 g (0.2 mol) of magnesium turnings, 30 ml of dry diethyl ether and a grain of iodine are placed in a one liter three-necked round-bottomed flask equipped with a condenser, a calcium chloride drying tube, a pressure equalizing funnel and a magnetic stirrer; the flask is purged with nitrogen, and 21.8 g (0.2 mol) of ethyl bromide in 30 ml of dry diethyl ether are then added. The mixture is then heated under reflux for one hour and left to cool. At ambient temperature, 16.51 g (0.12 mol) of 3-chlorobenzonitrile in 70 ml of dry diethyl ether are then added. A copious precipitate forms. The mixture is stirred overnight at ambient temperture and then cooled in an ice bath and hydrolyzed by slowly adding 50 ml of water and then about 100 ml of 6N hydrochloric acid until the pH is acid. The mixture is stirred for one and a half hours and then extracted with ethyl acetate. The organic extract is then washed twice with water, dried and concentrated on a rotary evaporator. This gives 26 g of an orange oil, which is concentrated in vacuo to give about 18.2 g of ochre crystals of 3'-chloropropiophenone melting at about 40° C.
13
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Rx-ID: 41448845 Find similar reactions
14
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Stage #1: propionyl chloride With AlCl3, aluminium chloride in 1,2-DICHLOROETHANE
T=0°C; 0.166667 h; Stage #2: chlorobenzene in 1,2-DICHLOROETHANE
T=0 - 50°C;
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Siddaraju, Yogesh; Prabhu, Kandikere Ramaiah
Organic and Biomolecular Chemistry, 2015 , vol. 13, # 48 p. 11651 - 11656 Title/Abstract Full Text View citing articles Show Details
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80%
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With phen; sodium t-butanolate in toluene
T=80°C; 3 h; Inert atmosphere;
Rx-ID: 41644851 Find similar reactions
Zheng, Hong-Xing; Xiao, Zu-Feng; Yao, Chuan-Zhi; Li, Qiang-Qiang; Ning, Xiao-Shan; Kang, YanBiao; Tang, Yong
Organic Letters, 2015 , vol. 17, # 24 p. 6102 - 6105 Title/Abstract Full Text View citing articles Show Details
15
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86%
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With methanol-d1; water-d2; potassium carbonate
T=20°C; Inert atmosphere of N2; Hide Experimental Procedure
Rx-ID: 28733379 Find similar reactions
CONCERT PHARMACEUTICALS, INC.
Patent: WO2009/105218 A2, 2009 ; Location in patent: Page/Page column 30-31 ; Title/Abstract Full Text Show Details
1:
A round-bottom flask was charged with 20 (5 g, 29.7 mmol) and MeOD (200 mL, 99.5 atom percent D methan(ol-d) (Sigma-Aldrich)) under N2. D2O (100 mL, 99.9 atom percent D deuterium oxide (Cambridge Isotopes)) was added slowly, followed by K2CO3 (820 mg, 5.93 mmol). The reaction was stirred at room temperature (rt) for 20 hours (h). The mixture was concentrated in vacuo nearly to dryness and then partitioned between EtOAc and D2O. The organic layer was washed with D2O (IX). The combined aqueous solutions were washed with EtOAc (IX). The combined organic layers <n="32"/>were dried (Na2SO4) and concentrated in vacuo to dryness to afford 4.32 g (86percent) of 21 as a white solid. The percentage of material deuterated at the 2 position was estimated to be 99percent by 1H NMR analysis. 1H NMR (CDCl3): δ 7.94-7.92 (m, IH), 7.85-7.81 (m, IH), 7.52 (m, IH), 7.40 (m, IH), 1.21 (s, 3H).
16
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Rx-ID: 40756141 Find similar reactions
With magnesium
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Li, Jian; Tian, Lei; Zhang, Chi; Chen, Liqin
Journal of Labelled Compounds and Radiopharmaceuticals, 2015 , vol. 58, # 10 p. 411 - 413 Title/Abstract Full Text View citing articles Show Details
A
B
17
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Rx-ID: 28733378 Find similar reactions
Stage #1: 1-bromo-3-chlorobenzene With n-butyllithium in diethyl ether; hexane
T=-40°C; Stage #2: N-methoxy-N-methyl-(propion-d5)amide in diethyl ether; hexane
T=-78 - -40°C; Hide Experimental Procedure
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CONCERT PHARMACEUTICALS, INC.
Patent: WO2009/105218 A2, 2009 ; Location in patent: Page/Page column 34-35 ; Title/Abstract Full Text Show Details
3:
A solution of 1- bromo-3-chlorobenzene (5.36 mL, 45.63 mmol) in Et2O (150 mL) was cooled to -40 °C. "-BuLi (20.6 mL of a 2.16 M solution in hexanes, 44.5 mmol) was added dropwise via syringe. The reaction was stirred for 15 min and then cooled to -78 °C. A solution of 25 (2.708 g, 22.2 mmol) in Et2O (44.6 mL) was added. After stirring for 5 min, the solution was warmed to -40 °C. After stirring for aproximately 1.5 h, the reaction was quenched with D2O (99.9 atom percent D (Cambridge Isotopes)), diluted with Et2O and warmed to rt. The mixture was partitioned between 1 N DCl in D2O and Et2O. The organic layer was washed with 1 N DCl (99 atom percent D in D2O (35 wt. percent, Sigma-Aldrich)) in D2O (2X) and 0.002 M Na2CO3 in D2O (IX), dried (Na2SO4), filtered and concentrated in vacuo. Purification via column <n="36"/>chromatography on an ISCO instrument (0 to 5percent EtOAc in hexane) provided 2.19 g (57percent) of 26 contaminated (15percent) with material undeuterated at the 2 position. This material was combined with other batches to afford 3.86 g (22.2 mmol) of 26 which was dissolved in MeOD (154 mL, 99.5 atom percent D (Sigma-Aldrich)). D2O (77 mL) and then K2CO3 (632 mg, 4.58 mmol) were added and the reaction was stirred overnight. The mixture was then concentrated under reduced pressure to near dryness and then partitioned between EtOAc and D2O. The organic layer was washed with D2O (IX). The combined aqueous solutions were washed with EtOAc (IX). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to dryness to afford 3.69 g (96percent) of 26 as a white solid. The percentage of material undeuterated at the 2 position was estimated to be 2percent by 1H NMR analysis. 1H NMR (CDCl3): δ 8.57 (s, IH), 8.40 (s, IH), 8.27 (s, IH), 7.35 (s, IH).
18
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With methanol-d1; water-d2; potassium carbonate
Hide Experimental Procedure
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Rx-ID: 28733382 Find similar reactions
CONCERT PHARMACEUTICALS, INC.
Patent: WO2009/105218 A2, 2009 ; Location in patent: Page/Page column 34-35 ; Title/Abstract Full Text Show Details
3:
A solution of 1- bromo-3-chlorobenzene (5.36 mL, 45.63 mmol) in Et2O (150 mL) was cooled to -40 °C. "-BuLi (20.6 mL of a 2.16 M solution in hexanes, 44.5 mmol) was added dropwise via syringe. The reaction was stirred for 15 min and then cooled to -78 °C. A solution of 25 (2.708 g, 22.2 mmol) in Et2O (44.6 mL) was added. After stirring for 5 min, the solution was warmed to -40 °C. After stirring for aproximately 1.5 h, the reaction was quenched with D2O (99.9 atom percent D (Cambridge Isotopes)), diluted with Et2O and warmed to rt. The mixture was partitioned between 1 N DCl in D2O and Et2O. The organic layer was washed with 1 N DCl (99 atom percent D in D2O (35 wt. percent, Sigma-Aldrich)) in D2O (2X) and 0.002 M Na2CO3 in D2O (IX), dried (Na2SO4), filtered and concentrated in vacuo. Purification via column <n="36"/>chromatography on an ISCO instrument (0 to 5percent EtOAc in hexane) provided 2.19 g (57percent) of 26 contaminated (15percent) with material undeuterated at the 2 position. This material was combined with other batches to afford 3.86 g (22.2 mmol) of 26 which was dissolved in MeOD (154 mL, 99.5 atom percent D (Sigma-Aldrich)). D2O (77 mL) and then K2CO3 (632 mg, 4.58 mmol) were added and the reaction was stirred overnight. The mixture was then concentrated under reduced pressure to near dryness and then partitioned between EtOAc and D2O. The organic layer was washed with D2O (IX). The combined aqueous solutions were washed with EtOAc (IX). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to dryness to afford 3.69 g (96percent) of 26 as a white solid. The percentage of material undeuterated at the 2 position was estimated to be 2percent by 1H NMR analysis. 1H NMR (CDCl3): δ 8.57 (s, IH), 8.40 (s, IH), 8.27 (s, IH), 7.35 (s, IH).
19
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Rx-ID: 40756142 Find similar reactions
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With magnesium
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Li, Jian; Tian, Lei; Zhang, Chi; Chen, Liqin
Journal of Labelled Compounds and Radiopharmaceuticals, 2015 , vol. 58, # 10 p. 411 - 413 Title/Abstract Full Text View citing articles Show Details
A
B
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20
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Rx-ID: 9181962 Find similar reactions
Stage #1: With lipase from Pseudomonas Cepacia
T=48°C; 77 h; Stage #2: With manganese(IV) oxide in dichloromethane
T=20°C;
Bustillo, Antonio J.; Aleu, Josefina; Hernandez-Galan, Rosario; Collado, Isidro G.
Tetrahedron Asymmetry, 2002 , vol. 13, # 15 p. 1681 - 1686 Title/Abstract Full Text View citing articles Show Details