Triethylamine → Methyl 3-Bromo-2-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-bromo-2-methylbenzoic acid (9.9 g,46 mmol) in thionyl chloride (20 mL) was heated to 60° C. for 1 hour, cooled to room temperature, and concentrated. The residue was suspended in 50 mL of methanol, cooled to 0° C., treated slowly with triethylamine (12.7 μL, 92 mmol), warmed to room temperature, and concentrated. The residue was partitioned between ethyl acetate and water and the organic phase was washed with saturated NaHCO3 and brine, dried (MgSO4), filtered, and concentrated to give 7.39 g of the desired product. Rf=0.5 (10% ethyl acetate/hexanes).

Provenance & Evidence