N-bromobutanimide → 5-Amino-2-bromo-4-methylbenzoic acid

Participants

Reaction Steps

A mixture of 3-amino-4-methylbenzoic acid (13) (5.1525 g, 34.08 mmol)) and DMF (30 mL) is cooled to about 5° C., whereupon N-bromosuccinimide (6.230 g, 35 mmol) is added in small portions, at a rate such that the reaction temperature stays below 10° C. The reaction mixture is then stirred at ambient temperature for about 3 hours and is then added to ice water (150 mL). The solids that form are filtered and dried to provide 3-Amino-6-bromo-4-methylbenzoic Acid (19) (6.5439 g, 83% yield).

Provenance & Evidence