Methanol → Methyl 4-bromo-3-methylbenzoate

Participants

Reaction Steps

Into a 10,000-mL 4-necked round-bottom flask was placed a solution of 4-bromo-3-methylbenzoic acid (500 g, 2.33 mol, 1.00 equiv) in methanol (5000 mL). This was followed by the addition of SOCl2 (556 g, 4.67 mol, 2.00 equiv) dropwise with stirring at <10° C. over 120 min. The resulting solution was heated to reflux for 5 h in an oil bath. The resulting mixture was cooled and concentrated under vacuum. This resulted in 535 g (crude) of methyl 4-bromo-3-methylbenzoate as a dark red solid.

Provenance & Evidence