N-bromobutanimide → 4-Bromo-2-methylpent-2-enoic acid methyl ester

Participants

Reaction Steps

A solution of 2-methylpent-2-enoic acid methyl ester (1.20 g, 9.37 mmol) and N-bromosuccinimide (1.83 g, 10.2 mmol) in dry carbon tetrachloride (15 mL) irradiated with a 250 W sunlamp so as to achieve a state of reflux for 2.5 hours. After cooling, the succinimide was filtered off, the carbon tetrachloride was evaporated, and the product was distilled over a short path under reduced pressure to give the title compound (1.60 g, 82%) as a colourless oil.

Provenance & Evidence