Reaction #324427

Reaction equation

4-bromo-2-fluoro-benzaldehyde

tert-butylamine

MgSO4

→

title compound

Yield 98.0%

(4-bromo-2-fluoro-benzylidene)-tert-butyl-amine

Yield 98.0%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Filtrationthe solution was filtered
2. 2
   Concentrationconcentrated

Procedure

To a CH2Cl2 (900 mL) solution of 4-bromo-2-fluoro-benzaldehyde (50.0 g, 246 mmol) was added tert-butylamine (42.3 mL, 29.3 g, 400 mmol) and MgSO4 (60.0 g, 499 mmol). After 48 h, the solution was filtered and concentrated to give 62.0 g (98%) of the title compound as a yellow liquid. 1H NMR (CDCl3): 8.48 (s, 1H), 7.89 (t, J=8.1 Hz, 1H), 7.32-7.25 (m, 2H), 1.29 (s, 9H).

Source