Vanillin → 5-Bromovanillin

Participants

Reaction Steps

To a solution of vanillin (30.40 g, 0.20 mol) in glacial acetic acid (200 mL) was added bromine (46.79 g, 0.29 mol) in glacial acetic acid (20 mL) at 10° over a period of 1 h. Additional acetic acid (100 mL) was added to the thickening mixture and the reaction was stirred for 24 h at ambient temperature. The reaction was diluted with ice/water (300 mL); the precipitate was filtered and washed well with water. A light beige solid (40.69 g, 89%) was obtained after vacuum drying: MS (ES) m/z 230.0. (M+H)+.

Provenance & Evidence