Hydrogen Bromide → 4-Bromo-2-ethylphenol

HRID 1597613Notes

Reaction equation

HRID 1597613 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])[CH3:2].[BrH:10].CS(C)=O>C(O)(=O)C.O>[Br:10][C:7]1[CH:6]=[CH:5][C:4]([OH:9])=[C:3]([CH2:1][CH3:2])[CH:8]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 69972-Ethylphenol

Product 1

HCID 878774-Bromo-2-ethylphenolYield 103%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 2-ethylphenol (8.97 g, 73.4 mmol) in acetic acid (100 ml) was added hydrobromic acid (48 wt. % solution in water; 50 ml, 442 mmol), DMSO (50 ml, 705 mmol) dropwise, and the mixture was stirred for 1 hour. The mixture was diluted with water, and the whole was extracted with diethylether. The organic layer was washed with saturated NaHCO3 aqueous solution, brine, dried over MgSO4, and concentrated in vacuo to give title compound (15.2 g, 99% yield). The compound was used for next reaction without purification.

Workup

  1. extractionthe whole was extracted with diethylether
  2. washThe organic layer was washed with saturated NaHCO3 aqueous solution, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6d6da113ff0540fda0430db88a022e30
Source dataset
uspto-grants-2001_09
Patent number
US06294558B1

Reaction notes

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