1,1'-Carbonyldiimidazole → 4-Bromo-2-fluoro-6-methylbenzamide

Participants

Reaction Steps

4-bromo-2-fluoro-6-methyl benzoic acid (200 g) was dissolved in 1 L of THF and treated portion wise with carbonyldiimidazole (180 g, 1.3 eq). The reaction mixture is stirred at ambient temperature for about 3 hours and then quenched by addition of aqueous ammonium hydroxide (400 ml). The resulting reaction mixture was stirred overnight at ambient temperature and then concentrated under reduced pressure to about 0.5 L volume. The resulting slurry was diluted by adding 1 L of water. The precipitated product was isolated by filtration, washed with water (3×300 ml), dried under vacuum at about 60° C. to obtain 174 g (87% isolated yield) of product.

Provenance & Evidence