N-bromobutanimide → Methyl 4-bromomethyl-2-methoxymethoxybenzoate

Participants

Reaction Steps

To a solution of methyl 2-methoxymethoxy-4-methylbenzoate (9.41 g, 0.0448 mol) in 150 mL of carbon tetrachloride was added N-bromosuccinimide (7.97 g, 0.0448 mol) and benzoyl peroxide (0.45 g, 0.002 mol). The reaction mixture was refluxed for 18 hours. The solid was filtered and the filtrate was concentrated in vacuo to give 13.2 g of an oil. The product was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane to give 10.2 g (79%) of product as an oil.

Provenance & Evidence