Hydrochloric Acid → 3-Bromocarbazole

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Reaction Conditions

Reaction Steps

A 250 ml, three-necked, round bottom flask was fitted with mechanical stirrer, addition funnel and reflux condenser (with drying tube). To the flask was added 16.7 g (0.10 mole) of carbazole and 100 ml of pyridine. The resulting mixture was stirred at 0° C. and 17.7 g (0.12 mole) of bromine was added dropwise over a period of 35 min. After stirring at 0° C. for an additional 1 hr, the resulting red mixture was poured into 600 ml of 3 N--HCl solution. The resulting precipitate was collected by filtration, washed with 200 ml of water, twice with 100 ml portions of 5% NaOH solution, and three times with 250 ml portions of water. The crude product was dissolved in 1500 ml of ether and dried over magnesium sulfate. Concentration of the ethereal solution gave 22.7 g (85% yield) of powder, m.p. 179°-183° C. Recrystallization three times from methanol gave 8.7 g of the desired product, m.p. 200°-201° C.

Provenance & Evidence