Triethylamine → 3-(4-Bromophenyl)-2-propenoyl azide

Participants

Reaction Steps

4-Bromocinnamic acid (7.45 g, 32.8 mmol) dissolved in acetone (150 mL) and stirred under nitrogen at 0° C. during addition of triethylamine (5.5 ml, 39.4 mmol), followed by ethyl chloroformate (3.76 ml, 39.4 mmol). Stirred reaction mixture at 0° C. for 1 hour, before adding a solution of sodium azide (3.19 g, 49.2 mmol) in water (16 mL) dropwise. Stirred reaction mixture at 0° C. for 1 hour, then room temperature for 1 hour, before pouring into water (1 L). The white precipitate was collected and washed repeatedly with water and dried (high vacuum, P2O5) to give 3-(4-bromophenyl)acryloyl azide (7.91 g, 31.3 mmol). 1H NMR (CDCl3) δ 7.66 (d, 1H), 7.55 (d, 2H), 7.40 (d, 2H), 6.41 (d, 1H). ESI MS (M+1)+: 251, 253 (Br).

Provenance & Evidence