Hydrogen Bromide → 4,4-Diphenyl-3-butenyl bromide

HRID 1741769Notes

Reaction equation

HRID 1741769 reaction equation
[CH:1]1([C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)O)[CH2:3][CH2:2]1.[BrH:18]>C1(C)C=CC=CC=1>[Br:18][CH2:3][CH2:2][CH:1]=[C:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 79850alpha-Cyclopropyl-alpha-phenylbenzenemethanol

Product 1

HCID 104017744,4-Diphenyl-3-butenyl bromideYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a vigorously stirred solution of 250.g (1.1 mol) of cyclopropyl diphenyl carbinol in 2.5 liters of toluene at ambient temperature was added rapidly 3.1 liters of 48% aqueous hydrobromic acid. After stirring for several hours, the layers were separated, the organic phase was washed with 1 liter of water, 1 liter of 10% aqueous sodium bicarbonate, and dried over sodium sulfate. The resulting crude oil residue was subjected to high-vacuum short path distillation to give 300 .g (95%) of 4-bromo-1,1-diphenyl-l-butene as a clear oil.

Workup

  1. customthe layers were separated
  2. washthe organic phase was washed with 1 liter of water, 1 liter of 10% aqueous sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. distillationThe resulting crude oil residue was subjected to high-vacuum short path distillation

Sources & evidence

ORD record
ord-56005fd3e6ce419890a8fa2aa28a41a7
Source dataset
uspto-grants-1994_08
Patent number
US05334720

Reaction notes

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