Acetic Acid → 2-Bromo-4-(2-nitroethenyl)phenol

Participants

Reaction Steps

3-Bromo-4-hydroxybenzaldehyde (20.1 g.) and n-propylamine (7.6 g.) were refluxed in dry benzene (150 ml.) using Dean-Stark water separator for 3 hours. Benzene phase was concentrated to get the crude aldimine as an oily product. The aldimine (24.2 g), nitromethane (24 ml.) and glacial acetic acid (72 ml.) were refluxed for 45 minutes. The reaction mixture was diluted with cold water. The solid was filtered off and crystallised from aqueous ethanol to obtain the title product; m.p. 132°-34° C.

Provenance & Evidence