Carbon tetrabromide → 3-(Tridec-1-ynyl)benzyl bromide

Participants

Reaction Steps

Triphenyl phosphine (1.5 g, 5.7 mmole) was added in small portions to a stirred solution of 3-(Tridec-1-ynyl)benzyl alcohol (1.34 g, 4.7 mmol, from example 34) and carbon tetrabromide (1.87 g, 5.7 mmole) in dichloromethane (20 ml) at 0° C., and the mixture was stirred for a further 3 hr at this temperature. After removing all the solvent under reduced pressure, n-hexane (20 ml) was added and the precipitate of triphenylphosphine oxide removed by filtration. Removal of the hexane under reduced pressure gave an oil which was distilled to give the desired product, (1.49 g, 91%) B.p. 170° C. at 0.05 mmHg., νmax 690, 790, 1210, 1460, 1480, 1600, 2220, 2850, 2920 cm-1, δ(CDCl3) 0.7 (3H, distorted t, terminal CH3), 1.2 (18H, m, alkylene chain), 2.16 (2H, t J=7 Hz, CH2 adjacent to acetylene), 4.15 (CH, s, benzylics), 7.06 (4H, m, aromatics).

Provenance & Evidence