N-bromobutanimide → 1-Bromo-2-(bromomethyl)naphthalene

Participants

Reaction Steps

1-Bromo-2-methyl naphthalene (25 g), N-bromosuccinimide (24.2 g), carbon tetrachloride (250 mL) and a catalytic amount of azo(bis)isobutylnitrile were refluxed 40 hours under a nitrogen atmosphere. The reaction was cooled to room temperature and volatile materials were removed in vacuo on a rotary evaporator. the residue was treated with hot hexane (steam bath, about 2×250 mL). The hexane solution was decanted and cooled in ice. The product was collected on a Buchner funnel and air dried to give 14.5 g of 1-bromo-2-bromomethylnaphthalene as white crystals.

Provenance & Evidence