N-bromobutanimide → 1-tert-Butyloxycarbonyl-2-bromo-4-(4-fluorophenyl)-5-(4-methylsulfonylphenyl)pyrrole

Participants

Reaction Steps

A suspension of 1-tert-butyloxycarbonyl-2-(4-methylsulfonylphenyl)-3-(4-fluorophenyl)pyrrole (13.5 g, 0.032 mole) in 100 ml N,N'-dimethylformamide was treated with a solution of N-bromosuccinimide (5.7 g, 0.032 mole) in 50 ml N,N'-dimethylformamide. The mixture was stirred for four hours at room temperature and poured into a mixture of 500 ml 5% sodium bicarbonate and 500 g of ice. The resulting solid was collected by filtration, washed with water, and dried. The crude product was recrystallized from diethyl ether/hexanes to yield 11.0 g (68%); m.p. 121° dec.

Provenance & Evidence