Bromine → HCID 19845921, compound

Participants

Reaction Steps

To a solution of 15 gm (0.084 mol) of hexahydrobenzoazocin-2-one (Chemica Scandinavia, 18, 191 (1964)) in 150 ml of chloroform at 0° C. was added 8.8 gm of PCl5 in small increments over a period of an hour. To this reaction mixture was added 70 mg of iodine, followed by the slow dropwise addition of 84 ml of a 1M solution of bromine in chloroform and this reaction mixture was warmed to room temperature and stirred for 1 hour, at which time it was concentrated at reduced pressure. A mixture of ice and water was added to the crude product and the mixture was extracted three times with methylene chloride. The combined organic fractions were filtered through MgSO4 and concentrated at reduced pressure. The solid bromide was recrystallized with a mixture of chloroform and hexanes to give 12 gm of pure 3-bromohexahydrobenzoazocin-2-one.

Provenance & Evidence