Bromine → Methyl 4-(bromomethyl)-3-methoxybenzoate

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Reaction Steps

A solution of methyl 3-methoxy-4-methylbenzoate (10 grams) and 2,2-azobis(2-methyl-propionitrile) (25 milligrams) in carbon tetrachloride (200 mL) was heated to gentle reflux. Bromine (9 grams) was added in portions and resulting solution was heated at reflux for 1 hour then stirred at room temperature overnight. The carbon tetrachloride was evaporated and the residue dissolved in ether. The ether solution was washed with water. The ether layer was dried over sodium sulfate then evaporated to give 13.9 grams of crude product. NMR (CDCl3) δ:3.92 (s, 3H), 4.45 (s, 2H), 7.65-7.00 (m, 3H).

Provenance & Evidence