N-bromobutanimide → 3-Bromo-7-(bromomethyl)-phenanthrene

Participants

Reaction Steps

A mixture of 3-bromo-7-methylphenanthrene (2.640 g, 9.736 mmol) and N-bromosuccinimide (1.733 g, 9.736 mmol) in 200 ml of carbon tetrachloride was heated to reflux and benzoyl peroxide (25 mg) was added. After 2.5 hour a starch-iodide test showed that no NBS remained and the mixture was cooled to room temperature, washed with water, dried (MgSO4) and evaporated to give 3.14 g of crude product as a solid. Flash chromatography through 330 g of silica gel (10% CH2Cl2 /hexane) gave 2.719 g of a white solid which was recrystallized from 70 ml of cyclohexane (reflux to RT) to yield 2.061 g (60%) of the title compound as a white solid, mp 147°-148° C.

Provenance & Evidence