2-Propenoic acid, 3-(2-fluoro-5-methoxyphenyl)-, (2E)- synthesis

Yield:476199-05-0 95%

Reaction Conditions:

with piperidine in pyridine at 110; for 2 h;

Steps:

(2E)-3- (2-Fluoro-5-methoxyphenyl)-2-propenoic acid

(2E)-3- (2-Fluoro-5-methoxyphenyl)-2-propenoic acid A solution of 2-fluoro-5-methoxybenzaldehyde (10.00 g, 64.9 MMOL), malonic acid (13.4 g, 128.8 mmol), piperidine (2.00 ML) and pyridine (100 mL) was heated to 110C for 2h. After this time the solvent was removed in vacuo and the residue taken up in ethyl acetate and washed with aqueous hydrochloric acid (2N, 100 ML). The organic solvent was dried (MGSO4) and the solvent evaporated IN VACUO. The solid was recrystallised from hot ethanol to give a white solid (12.2 g, 95%) ; ON (300 MHz, DMSO) 7.60 (1H, d, J 7HZ, CH=C), 7.31-7. 28 (1H, m, Ar), 7.20 (1H, t, Ar), 7.07-6. 97 (1H, m, Ar), 6.62 (1H, d, J 8Hz, CH=CH), 3.80 (3H, s, OCH3).

References:

WO2004/43903,2004,A1 Location in patent:Page 42 - 43