Hydrogen Bromide → 3-Iodophenethyl bromide

HRID 1534422Notes

Reaction equation

HRID 1534422 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6]O.[BrH:11]>O>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][CH2:6][Br:11]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 151698502-(3-Iodophenyl)ethanol

Product 1

HCID 217088003-Iodophenethyl bromideYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-iodophenethyl alcohol (see Preparation 26) (1.2 g) and 48% aqueous hydrobromic acid (20 ml) was stirred at room temperature for 8 hours, poured into water and extracted into methylene chloride. The organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and water, dried over sodium sulphate and evaporated to give the title compound as a pale brown oil (1.1 g, 73%), which was characterised by its 1H-n.m.r. spectrum.

Workup

  1. extractionextracted into methylene chloride
  2. washThe organic extracts were washed with saturated aqueous sodium hydrogen carbonate solution and water
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-f6802531df9946fcb7a4d243ea4f90f3
Source dataset
uspto-grants-1992_02
Patent number
US05089505

Reaction notes

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