Carbon Tetrachloride → 2-(8-Bromonaphthalen-1-yl)acetonitrile

Participants

Reaction Steps

According to the procedure of A. Mizuno, et al. Synthesis 1007 (1980), a mixture of 8-bromo-2-hydroxymethylnaphthalene (1.70 g, 7.17 mmol), KCN (0.93 g, 14.34 mmol) and 18-crown-6 (0.19 g, 0.72 mmol) in acetonitrile (24 mL) was stirred at room temperature for 15 minutes. A mixture of n-Bu3P (1.60 g, 7.89 mmol) and acetonitrile (7 mL) was added. The mixture was cooled to 0° C., and a solution of CCl4 (1.21 g, 7.89 mmol) in acetonitrile (7 mL) was added. The resulting mixture was stirred at room temperature for two days. Ether (300 mL) was added and the mixture was washed with 10% aqueous citric acid (150 mL). CCl4 (20 mL) was added and the mixture was washed with H2O (2×150 mL); saturated aqueous NaCl (150 mL), dried (MgSO4), and concentrated. The crude material was purified by flash chromatography (eluant EtOAc/hexane (5:95), to EtOAc/hexane (20:80)) to give a yellow solid (1.13 g, 64%), m.p. 55°-56° C.

Provenance & Evidence