Sulfuric Acid → 7-Bromomethylnaphthalene-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

Isobutylene was passed through a suspension of 7-bromomethylnaphthalene-1-carboxylic acid (10.4 g, 39.2 mmol) in dichloromethane (150 mL) in the presence of concentrated sulfuric acid (1 mL) for 3 hours, and then the mixture was stirred overnight. The resulting deep green solution was washed with a saturated solution of sodium hydrogen carbonate, dried (magnesium sulfate) and the solvent was removed under reduced pressure to give crude 7-bromomethylnaphthalene-1-carboxylic acid tert-butyl ester (11.2 g, 88.8%) as a deep green oil. This compound was directly used for the subsequent Michaelis-Becker alkylation without further purification.

Provenance & Evidence