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

HRID 867113Notes

Reaction equation

HRID 867113 reaction equation
C(N(CC)[CH2:4][C:5]#[C:6][C@@H:7]([O:13][C:14](=[O:16])[CH3:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])C.N#C[Br:21]>CCOCC>[Br:21][CH2:4][C:5]#[C:6][C@@H:7]([O:13][C:14](=[O:16])[CH3:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 227938191-Diethylamino-4(S)-acetyloxy-2nonyne

Product 1

HCID 227938171-Bromo-4(S)-acetyloxy-2-nonyneYield 65.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  1. washThe resulting solution is washed with 5% hydrochloric acid, water, and saturated aqueous brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customAfter evaporating the filtrate
  5. distillationthe residual oil is distilled

Sources & evidence

ORD record
ord-60d6244aef1746718da25bc64b831093
Source dataset
uspto-grants-1978_07
Patent number
US04102888

Reaction notes

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