Cyanogen Bromide → 1-Bromo-4(S)-acetyloxy-2-nonyne

Participants

Reaction Steps

A solution of 1-diethylamino-4(S)-acetyloxy-2-nonyne (50.6 g., 0.20 mole) and cyanogen bromide (21.2 g., 0.20 mole) in ether (250 ml.) is allowed to stand at 25° to 27° C. for 18 hours. The resulting solution is washed with 5% hydrochloric acid, water, and saturated aqueous brine, dried over sodium sulfate, and filtered. After evaporating the filtrate, the residual oil is distilled to provide the title compound (34.1 g., 65%), b.p. 97°-105° C./0.2 mm.; [α]D26 -83° (C 3.7, CHCl3).

Provenance & Evidence