Acetyl chloride → Methyl 5-amino-2-bromobenzoate

Participants

Reaction Conditions

Reaction Steps

Acetyl chloride (29.2 ml, 32.2 g, 410.7 mmol) was added dropwise to methanol (210 ml) at 0-10° C. under nitrogen atmosphere and the solution was stirred for 30 min at 0° C. After addition of 5-acetamido-2-bromobenzoic acid (21.2 g, 82.1 mmol) in methanol at 0° C. the solution was stirred for 3 h at 55° C. After evaporation of methanol ethyl acetate (160 ml) was added and stirring was continued for 1 h at room temperature. The precipitation was filtered off and it was dissolved in water. pH was adjusted to 8 with NaHCO3. The mixture was extracted with ethyl acetate, washed with water, dried over Na2SO4 and concentrated under vacuum.

Provenance & Evidence