Reaction #64307

Reaction equation

4-bromobenzaldehyde

2,4-dimethylpent-3-ylamine

water

→

(4-bromobenzylidene)(1-isopropyl-2-methylpropyl)amine

Yield 94.9%

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Otherwas removed with a Dean-Stark trap
3. 3
   OtherThe toluene then was removed under vacuum and distillation of the remaining residue

Procedure

A mixture of 4-bromobenzaldehyde (7.3 g, 40.0 mmol), 2,4-dimethylpent-3-ylamine (4.8 g, 41.4 mmol), and para-toluenesulfonic acid (0.05 g, 0.29 mmol) in 125 mL of toluene was heated under reflux while water was removed with a Dean-Stark trap. The toluene then was removed under vacuum and distillation of the remaining residue gave (4-bromobenzylidene)(1-isopropyl-2-methylpropyl)amine (10.71 g) as a clear colorless oil.

Source