Cyanogen Bromide → 1-Bromo-4-acetoxy-2-nonyne
Reaction equation
C(N(CC)[CH2:4][C:5]#[C:6][CH: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][CH:7]([O:13][C:14](=[O:16])[CH3:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-diethylamino-4-acetoxy-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°-27° for 18 hours. The ether solution is washed with 5% hydrochloric acid solution, water, and brine and dried over sodium sulfate. The ether is evaporated and the residual oil distilled. After a forerun of diethylcyanamide, there is collected 34.1 g. (65%) of 1-bromo-4-acetoxy-2-nonyne, b.p. 97°-105°/0.2 mm.
Workup
- washThe ether solution is washed with 5% hydrochloric acid solution, water, and brine
- dry with materialdried over sodium sulfate
- customThe ether is evaporated
- distillationthe residual oil distilled
- customAfter a forerun of diethylcyanamide, there is collected 34.1 g
Sources & evidence
- ORD record
- ord-10666252a1da49a4a25827b8813ba3e7
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04091107
Reaction notes
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