4-(Bromomethyl)benzoic acid → 4-(Azidomethyl)benzoic acid

Participants

Reaction Steps

To a stirred solution of p-bromomethylbenzoic acid (13.607 g, 63.3 mmol) in acetone (300 ml) and H2O (15ml) was added dropwise at room temperature a solution of NaN3 (4.123 g, 63.4mmol) in H2O (40 ml). The reaction mixture was stirred at room temperature overnight (ca 20 h). After evaporation of the acetone, the residual solid was suspended in water and filtered, yielding 10.13 g (57.2 mmol, 90.3%) of p-azidomethylbenzoic acid as a white powder: 1Hmr (DMSO-d6 δ: 4.57 (2H, s, --CH3N3), 7.43-7.55-7.93-8.07 (4H, A2'B2', aromatic Hs) and 12.7 ppm (br, s, --CO2H): ir (nujol) νmax : (--N3) and 1670 cm-1 (--CO2H).

Provenance & Evidence