Triphenylphosphine → HCID 18796385, compound

Participants

Reaction Steps

3-Bromo-4-(trifluoroacetamido)anisole (4.7 g, 0.16 mol) was suspended in carbon tetrachloride (60 ml) and triphenylphosphine (6.2 g, 0.024 mol) was added. The reaction was heated at reflux for 12 hours. The reaction was allowed to cool to ambient temperature, and filtered. The solid was washed thoroughly with ethyl acetate:diethyl ether (1:1, 200 ml:200 ml). The filtrate was concentrated in vacuo to afford a red solid. This solid was dissolved in N,N-dimethylformamide (10 ml) and this solution was added to sodium azide (1.55 g, 0.024 mol). The reaction was stirred at ambient temperature for 12 hours, and diluted with water (100 ml). The product was extracted into ethyl acetate (3×50 ml) and the combined organics were washed with brine (100 ml), dried over magnesium sulphate and the solvent removed in vacuo. Chromatography on silica eluting with 10% ethyl acetate in hexane afforded the title compound as a pale orange solid (4.2 g, 66%), m/z (ES+) 323 (M+ +H, 100%). 1H NMR (250 MHz, CDCl3) δ 3.92 (3H, s), 7.03 (1H, dd J 2.7 Hz, J 8.8 Hz), 7.30 (1H, d, J 2.7 Hz), 7.34 (1H, d, J 8.8 Hz).

Provenance & Evidence