3-Bromo-4-aminotoluene hydrochloride

Bromo-4-aminotoluene hydrochloride. Transfer the partially dried 3-bromo-4-acetaminotoluene to a 1 5-litre round-bottomed flask, add 250 ml. of rectified spirit, and reflux on a water bath until the sohd dissolves completely. Introduce through the condenser 250 ml. of concentrated hydrochloric acid to the boihng solution and continue the refluxing for a further 3 hours. During this time crystals of 3-bromo-4-aminotoluene hydrochloride separate. Pour the hot mixture into a 1-Utre beaker and cool thoroughly. Filter the crystals of the hydrochloride at the pump through a Buchner funnel and wash rapidly with two 50 ml. portions of chilled rectified spirit. The yield of the hydrochloride is 150 g. 

Bromo-4-aminotoluene, Suspend the hydrochloride in 400 ml, of water in a 1-Utre beaker equipped with a mechanical stirrer. Add a solution of 70 g. of sodium hydroxide in 350 ml. of water. The free base separates as a dark heavy oil. After cooUng to 15-20°, transfer the mixture to a separatory funnel and run off the crude 3-bromo-4-amino-toluene. This weighs 125 g. and can be used directly in the next step (3). 

The partially dried 3-bromo-4-acetaminotoluene is refluxed with 500 cc. of 95 per cent ethyl alcohol in a 3-I. round-bottom flask. To the boiling solution is added 500 cc. of concentrated hydrochloric acid and the refluxing is continued for three hours. During this time, crystals of the hydrochloride of 3-bromo-4-aminotoluene separate. The hot mixture is poured into a 2-I. beaker and cooled thoroughly in running water. The hydrochloride is filtered by suction and washed rapidly with two loo-cc. portions of chilled alcohol. The weight of the hydrochloride is 2501-300 g. (Note 4). 

Bromo-4-acetaminotoluene, 593, 605 p-Bromoacetanilide, 577, 580 p - Bromoace tophenone. 726, 732 m-Bromo-p-acetotoluidido, 593, 605 3-Bromo-4-aminotoluene, 593, 605 hydrochloride, 605 p-Bromoanilides, 361 p-Bromoaniline, 577, 580 o-Bromoanisole, 404 p-Bromobenzaldehyde, 689, 694, 696 diacetate, 696... 

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