Query Query O
1. Query
O
O
Results
Date
11 reactions in Reaxys
2016-05-03 19h:15m:52s (EST)
O
O
O
O
Search as: As drawn, No salts, No mixtures
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
1/5
2016-05-03 19:19:08
O
O
O
N
O
O O
O
O
Rx-ID: 3342485 View in Reaxys 1/11 Yield
Conditions & References
98 %
With phosphoryl chloride Maccarone, Emanuele; Cuffari, Giuseppe; Passerini, Amedeo; Raymo, Francisco; Journal of Chemical Research, Miniprint; nb. 9; (1991); p. 2401 - 2413 View in Reaxys
98 %
8 :Example 82,4,6-Trimethoxy-benzaldehyde2,4,6-Trimethoxy-benzene (40gm, 0.22x103 mmol) was added to dimethylformamide and stirred at a temperature in the range of -5 to 0°C under N2 atmosphere, followed by addition of phosphorus oxychloride (48 gm, 0.5x103 mmol) drop wise over a period of 30-45 minutes. The reaction mixture was stirred for one hour at 0°C, poured over crushed ice followed by saturated sodium carbonate solution. Precipitate obtained was filtered and washed with water to obtain the title compound.Yield: 46 gm (98percent); 1 HNMR (CDCI3): δ 10.35 (s, 1 H), 6.67 (s, 2H), 3.88 (s, 6H), 3.87 (s, 3H); MS: m/e 197 (M+1 ). With phosphoryl chloride, T= -5 - 0 °C , Inert atmosphere Patent; PIRAMAL LIFE SCIENCES LIMITED; BANDGAR, Babasaheb Pandurang; TOTRE, Jalindar Vasant; WO2011/121505; (2011); (A1) English View in Reaxys
98 %
With phosphoryl chloride, Time= 1.75h, T= 0 °C , Vilsmeier-Haack Formylation Nenikis, Algirdas; Stonius, Sigitas; European Journal of Organic Chemistry; vol. 2015; nb. 28; (2015); p. 6359 6369 View in Reaxys
92 %
With phosphoryl chloride, Time= 16h, T= 20 °C , Vilsmeier Reaction Huang, Yu; Gan, Haifeng; Guo, Kai; Journal of Chemical Research; vol. 39; nb. 8; (2015); p. 458 - 461 View in Reaxys
91 %
With phosphoryl chloride, Inert atmosphere, Vilsmeier-Haack Formylation Sum, Tze Han; Sum, Tze Jing; Stokes, Jamie E.; Galloway, Warren R.J.D.; Spring, David R.; Tetrahedron; vol. 71; nb. 26-27; (2015); p. 4557 - 4564 View in Reaxys
78 %
With phosphoryl chloride, Time= 1h, T= 0 °C , Inert atmosphere Ikawa, Takashi; Kaneko, Hideki; Masuda, Shigeaki; Ishitsubo, Erika; Tokiwa, Hiroaki; Akai, Shuji; Organic and Biomolecular Chemistry; vol. 13; nb. 2; (2015); p. 520 - 526 View in Reaxys
36.9 g
With phosphoryl chloride, Time= 1.5h, Ambient temperature Sargent, Melvyn V.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1982); p. 403 - 411 View in Reaxys
O
O
O
Cl
O O
Cl O
O O
Rx-ID: 39884141 View in Reaxys 2/11
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
2/5
2016-05-03 19:19:08
Yield
Conditions & References
44 %
3.2. General Formylation Procedure General procedure: The appropriate benzene derivative (3.2–10.6 mmol) was dissolved in dry DCM (10–20 mL), purged with Ar, and cooled with an ice bath to 0 °C. Next, TiCl4 (2.2 eq.) was added dropwise. The reaction mixture was stirred for 1 h. Afterwards, dichloromethyl methyl ether (1.1 eq.) was added, and the mixture was left to react for a further 45 min. As a reaction quencher, a saturated solution of NH4Cl (25 mL) was added. The mixture was then left for 2 h. The organic layer was separated and washed with 0.1 N HCl solution (3 × 50 mL) and brine (3 × 50 mL). The organic layer was dried over MgSO4 and filtered, and the solvent was evaporated under vacuum to furnish the desired aldehydes (Figure 1). The purified products were homogeneous by HPLC and were characterized and purified by using various physical techniques. Stage 1: With titanium tetrachloride in dichloromethane, Time= 1h, T= 0 °C , Inert atmosphere Stage 2: in dichloromethane, Time= 0.75h, T= 0 °C , Inert atmosphere, regioselective reaction Ramos-Tomillero, Ivn; Parads-Bas, Marta; De Pinho Ribeiro Moreira, Ibrio; Bofill, Josep Mara; Nicols, Ernesto; Albericio, Fernando; Molecules; vol. 20; nb. 4; (2015); p. 5409 - 5422 View in Reaxys
O
O
O
Cl
O
O O
Cl
O
O
O
O
O O
O
Rx-ID: 35445058 View in Reaxys 3/11 Yield 65 %, 4 %
Conditions & References With silver trifluoromethanesulfonate in dichloromethane, Time= 0.25h, T= 0 °C , Inert atmosphere Ohsawa, Kosuke; Yoshida, Masahito; Doi, Takayuki; Journal of Organic Chemistry; vol. 78; nb. 7; (2013); p. 3438 - 3444 View in Reaxys
O
N
HO
O
O
O
O
O
O
O O
O
I
O
Rx-ID: 33465203 View in Reaxys 4/11 Yield 55 %, 44 %
Conditions & References 4.3. Typical procedure for one-pot conversion of aromatic bromides into aromatic methyl esters with DMF General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of pbromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82percent yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil. Stage 1: With n-butyllithium in tetrahydrofuran, hexane, Time= 0.5h, T= -78 °C Stage 2: in tetrahydrofuran, hexane, Time= 2h, T= -78 - 20 °C Stage 3:, Further stages Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 68; nb. 24; (2012); p. 4701 - 4709 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
3/5
2016-05-03 19:19:08
O
O
O
O O O
O
Rx-ID: 34041743 View in Reaxys 5/11 Yield
Conditions & References Vilsmeier-Haack Formylation Bandgar, Babasaheb P.; Hote, Baliram S.; Jalde, Shivkumar S.; Gacche, Rajesh N.; Medicinal Chemistry Research; vol. 21; nb. 10; (2012); p. 3006 - 3014 View in Reaxys
O
O
O
O N
O
O
O O
O
O
Cl
O
O
O O O
OO
O
Rx-ID: 28202322 View in Reaxys 6/11 Yield
Conditions & References
33 %, 22 %
With AlCl3, aluminium chloride in chlorobenzene, Time= 22h, T= 0 - 18 °C Kantlehner, Willi; Anders, Ernst; Mezger, Jochen; Stoyanov, Edmont V.; Kress, Ralf; Wermann, Kurt; Frey, Wolfgang; Goerls, Helmar; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 63; nb. 4; (2008); p. 395 - 406 View in Reaxys
O
O
O
C
N O O
O
O
Rx-ID: 11167311 View in Reaxys 7/11 Yield
Conditions & References
77 %
Stage 1: With aluminium trichloride in toluene, Time= 15h, T= 20 °C Stage 2: With water in toluene, Time= 2h, T= 20 °C , Further stages. Tobisu, Mamoru; Yamaguchi, Seiji; Chatani, Naoto; Organic Letters; vol. 9; nb. 17; (2007); p. 3351 - 3353 View in Reaxys
O
O
O
N O O
O O O
Rx-ID: 9895372 View in Reaxys 8/11 Yield 85 %
Conditions & References With trichlorophosphate, T= 40 - 50 °C , Vilsmeier reaction Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.; Journal of Medicinal Chemistry; vol. 48; nb. 7; (2005); p. 2407 - 2419 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
4/5
2016-05-03 19:19:08
-1 O
F
O
O
(v4)
F
B FF
O
O+
O O
O
O
Rx-ID: 1745236 View in Reaxys 9/11 Yield
Conditions & References With water, 1.) CH2Cl2, 0 deg C, 0.5 h, 2.) CH2Cl2, 20 deg C, 1 h, Yield given. Multistep reaction Pindur, U.; Flo, C.; Journal of Heterocyclic Chemistry; vol. 26; (1989); p. 1563 - 1568 View in Reaxys
O
O
O
HN
O O
O O
O
Rx-ID: 827117 View in Reaxys 10/11 Yield
Conditions & References With diethyl ether, trichlorophosphate, anschliessend Behandeln des Reaktionsprodukts mit wss. NaOH Kenyon; Mason; Journal of the Chemical Society; (1952); p. 4964,4966 View in Reaxys
O
O
O
O
N
O O
O
Rx-ID: 120998 View in Reaxys 11/11 Yield
Conditions & References With hydrogenchloride, zinc(II) chloride, benzene, Reaktion des entstandenen Aldimids mit waessr. Salzsaeure Herzig; Wenzel; Gehringer; Monatshefte fuer Chemie; vol. 24; (1903); p. 866 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
5/5
2016-05-03 19:19:08