Methyl Acrylate → HCID 15453700, compound

Participants

Reaction Conditions

Reaction Steps

A 100 ml 3-neck flask with magnetic stirrer was charged with 2-bromo-4-(trifluoromethyl)aniline (500 mg, 2.08 mmol), methyl acrylate (538 mg, 6.25 mmol), Pd(OAc)2 (23.3 mg, 0.104 mmol), P(o-tolyl)3 (64 mg, 0.21 mmol), triethylamine (422 mg, 4.7 mmol) and acetonitrile (20 ml). The flask was purged with N2 and heated to 90° C. overnight. Saturated aqueous NH4Cl (40 ml) was added, and the mixture was extracted with ethyl acetate (10 ml*3). The organic layer was dried over Na2SO4, filtered, and concentrated to dryness. The crude product was purified by silica gel chromatography to give (E)-methyl 3-(2-amino-5-(trifluoromethyl)phenyl)acrylate (185.9 mg, 36.5%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.69 (d, J=16 Hz, 1H), 7.53 (s, 1H), 7.32 (d, J=8.8 Hz, 1H), 6.67 (d, J=8.8 Hz, 1H), 6.34 (d, J=16 Hz, 1H), 4.20 (s, 2H), 3.74 (s, 3H).

Provenance & Evidence