Hydrogen Bromide → 82455-06-9

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-fluoroaniline (27.75 g), acetone (500 ml) and hydrobromic acid (80 ml, 48%) stirred at -5° C. was treated over 30 minutes with a solution of sodium nitrite (21.0 g) in water (50 ml). Methyl acrylate (215 g) and cuprous bromide (0.04 g) were added. The internal temperature was allowed to rise in a carefully controlled manner; at 15° C. the evolution of N2 was vigorous. When the rate of N2 evolution decreased, the mixture was stirred at 25° C. for 1 hr to complete the reaction. The mixture was evaporated, and the residue was partitioned between water and toluene to give crude methyl 2-bromo-3-(4-fluorophenyl)propionate.

Provenance & Evidence