Carbon tetrabromide → HCID 19025816, compound

Participants

Reaction Steps

Part A. A solution of N-(5-hydroxypentyl)-5-bromopentanamide (4.07 g, 15.3 mmol) and carbon tetrabromide (7.61 g, 22.9 mmol) in methylene chloride (75 mL) was cooled to 0° C., and treated with a solution of triphenylphosphine (6.02 g, 22.9 mmol) in methylene chloride (30 mL) dropwise. After stirring for 12 hours, the reaction mixture was evaporated, and the residual oil was separated by flash chromatography (1:1 ethyl acetate-hexane) to afford the oily product, N-(5-bromopentyl)-5-bromopentanamide (1.69 g, 5.14 mmol, 34%). 1H NMR (CDCl3): 5.96 (1H, br s); 3.40 (4H, t, J=6.6 Hz); 3.24 (2H, q, J=6.2 Hz); 2.20 (2H, t, J=7.0 Hz); 1.94-1.74 (6H, m); 1.58-1.42 (4H, m).

Provenance & Evidence