Bromine → 4-Chlorobenzonitrile

Participants

Reaction Steps

To a 25 ml three-necked flask equipped with an equal pressure additional funnel, a dry-ice condenser with a gas outlet and a stopper, is charged 14.2 g (0.1 mole) of 1-chloro-4-cyanocyclo-hex-1-ene (I) and 3 g of chlorobenzene The mixture is heated to 90°-100° C. with stirring. Bromine, 32 g (0.2 mole), is added dropwise, sub-surface. The reddish-brown color dissipates quickly and a gas evolution occurs. When approximately 24 g of bromine has been added, the pot temperature is raised to 120°-130° C. The remaining bromine is added in the same fashion. The pot temperature may then be raised to 150°-160° C. for 2-4 hours. During this period, an additional amount of bromine, such as about 1-2 g, may be added to complete the conversion of (I). A good yield of 4-chlorobenzonitrile will be obtained by the fractional distillation of the mixture.

Provenance & Evidence