Cyanogen Bromide → 1-Bromo-4-acetoxy-2-nonyne

HRID 1833775Notes

Reaction equation

HRID 1833775 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

HCID 10476Cyanogen BromideHCID 213175261-Diethylamino-4-acetoxy-2-nonyne

Product 1

HCID 203861201-Bromo-4-acetoxy-2-nonyne

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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

  1. washThe ether solution is washed with 5% hydrochloric acid solution, water, and brine
  2. dry with materialdried over sodium sulfate
  3. customThe ether is evaporated
  4. distillationthe residual oil distilled
  5. customAfter a forerun of diethylcyanamide, there is collected 34.1 g

Sources & evidence

ORD record
ord-fea23b6389d148618c764eb876ff0aa2
Source dataset
uspto-grants-1978_01
Patent number
US04066692

Reaction notes

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