N-bromobutanimide → 2-acetoxy-1-acetyl-5-bromomethyl-1H-imidazole-4-carboxylic acid methyl ester

Participants

Reaction Steps

To a solution of 4b (9.0 g, 38 mmol) in 300 mL of CCl4 was added N-bromosuccinimide (7.1 g, 40 mmol) and benzoyl peroxide (80 mg). The solution was refluxed for 4 h and then cooled down to rt. Succinimide was then removed through filtration and the filtrate was concentrated to provide 2-acetoxy-1-acetyl-5-bromomethyl-1H-imidazole-4-carboxylic acid methyl ester 4c (12 g, 95%). MS (ESI+) (M+1)=318.9, 320.9.

Provenance & Evidence