Glycine → N-[(4-Bromophenyl)methyl]glycine

Participants

Reaction Steps

To water (40 ml) was added glycine (246 mmol, 18.5 g) and aqueous sodium hydroxide (10M; 100 mmol, 10 ml). 4-Bromobenzaldehyde (130 mmol, 24 g) was added to afford a suspension. Ethanol (40 ml) and THF (90 ml) were added, followed by sodium borohydride (174 mmol, 6.6 g) and the mixture stirred at room temperature overnight. The reaction mixture was concentrated and washed with ether (×3) and the aqueous layer acidified to pH ˜6.5 at which point precipitation occurred. The solid was filtered and washed with water and diethyl ether before co-evaporation with toluene to give 2-(4-bromobenzylamino)acetic acid (7H2) 11.3 g; 1H NMR (400 MHz, DMSOd6) δ 7.56 (d, 2H) 7.38 (d, 2H) 3.85 (s, 2H) 3.10 (s, 2H).

Provenance & Evidence