Hexane → 3-(Bromomethyl)-5-fluoro-1-benzothiophene

Participants

Reaction Steps

5-Fluoro-3-methyl-benzo[b]thiophene (1.7 g, 10.24 mmol) was reacted with N-bromo succinimide (2 g, 1126 mmol) and benzoyl peroxide (2 mg) in CCl4 (15 mL). The resulting reaction mass was refluxed using photoelectric radiation. The reaction was monitored by TLC (100% hexane). The reaction mass was quenched with water and separated the CCl4 layer. The aqueous layer was extracted with chloroform and the organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated. Purification by column chromatography on silica gel (100% hexane) afforded 1.3 g of the product (52% yield).

Provenance & Evidence