N-ethyl carbazole → 3,6-Bis(4-chlorobutyryl)-N-ethylcarbazole

Participants

Reaction Steps

To a solution of 78.0 g (0.4 mole) of 9-ethylcarbazole and 141 g (1.0 mole) of 4-chlorobutyryl chloride in 1 liter of methylene chloride, which has been previously chilled to 0°C, is added portionwise 127.0 g (0.95 mole) of aluminum chloride. The mixture is stirred at room temperature for 16 hours, and the resulting complex is decomposed with a concentrated hydrochloric acid-ice mixture. The organic layer is separated, washed with water, dried over magnesium sulfate and pentane added to precipitate the desired product. Recrystallization from acetone followed by a recrystallization from an acetone methanol solution results in the formation of 3,6-bis (4-chlorobutyryl)-9-ethylcarbazole, m.p. 106°-8°C; λmaxEtOH 259; and E1cm1% 1030.

Provenance & Evidence