Carbon tetrabromide → HCID 14797061, compound

Participants

Reaction Steps

The alkynyl ether 16 (5.62 g, 0.0191 mol) in dichloromethane (150 ml) at 0° C. was treated successively with carbon tetrabromide (8.23 g, 0.0248 mol) and triphenylphosphine (13 g, 0.050 mol) and stirred for 5 h at r.t. The solution was treated with silica gel, the solvent removed invacuo and the dry residue loaded onto a prepared flash column. Elution with hexanes yielded the pure bromide 17 (87% from 15); δH (270 MHz, CDCl3) 1.10 (3H, t, J 7.4), 1.27-1.54 (14H, m), 1.84 (2H, quin, J 7.3), 2.15 (4H, m) and 3.40 (2H, t, J 6.8). δC (100 MHz, CDCl3) 12.82, 14.79, 27.28, 29.23, 29.26, 29.4, 29.53, 29.80, 29.80, 30.11, 33.04, 79.96 (quartenary) and 82.00 (quartenary).

Provenance & Evidence