Tert-Butylamine → (4-Bromo-2-fluoro-benzylidene)-tert-butyl-amine

Participants

Reaction Steps

A mixture of 4-bromo-2-fluorobenzaldehyde (10 g, 47 mmol), tert-butyl amine (6.1 mL, 57 mmol) and 4 Å powder molecular sieves (8.0 g) in 160 mL CH2Cl2 (160 mL) was stirred at rt for 18 h. The reaction mixture was filtered through a pad of celite and concentrated to give the title compound (9.9 g, 78%). MS (ESI): mass calcd. for C11H13BrFNO, 258.1; m/z found, 260.0 [M+H]+. 1H NMR (CDCl3): 10.32 (s, 1H), 8.48 (s, 1H), 7.89 (t, J=8.1 Hz, 1H), 7.50-7.20 (m, 1H), 1.49-1.08 (m, 9H).

Provenance & Evidence