Water → HCID 53849939, compound

Participants

Reaction Steps

3-Bromobenzaldehyde (23.7 g, 128.2 mmol), N-acetyl glycine (10.0 g, 85.5 mmol) and sodium acetate (5.26 g, 64.1 mmol) in acetic anhydride (60 mL) was heated to reflux for 1 h. The reaction was cooled to room temperature and water (100 mL) was added. The resulting suspension was filtered and the solid was washed with water (2×50 mL). The remaining solid was dissolved in methylene chloride (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow solid. The solid was suspended in dry MeOH (200 mL) and heated to reflux for 9 h. The reaction mixture was concentrated in vacuo to give a yellow solid. Recrystallization from EtOAc and petroleum ether gave methyl m-bromo-α-acetamidocinnamate as a yellow solid. MS (CI) m/z 298 (M++1 (Br=79), 100%), 300 (M++1 (Br=81), 100%). 13C NMR (50 MHz, d6-DMSO): δ23.3, 52.8, 122.5, 125.0, 128.06, 130.0, 130.2, 132.2, 132.3, 135.9, 165.4 and 168.8.

Provenance & Evidence