Hydrogen Bromide → 1-(3,5-Difluoro-4-hydroxyphenyl)ethan-1-one

HRID 221832Notes

Reaction equation

HRID 221832 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=[C:6]([F:10])[C:7]=1[O:8]C.Br>O>[F:1][C:2]1[CH:3]=[C:4]([C:11](=[O:13])[CH3:12])[CH:5]=[C:6]([F:10])[C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 27369833',5'-Difluoro-4'-methoxyacetophenone

Product 1

HCID 151513381-(3,5-Difluoro-4-hydroxyphenyl)ethan-1-oneYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(3,5-difluoro-4-methoxyphenyl)ethanone (12 g, 64.5 mmol) and 48% aqueous HBr (32 mL) was stirred at reflux for 30 h. The reaction was cooled to rt and diluted with water and the aqueous layer was extracted twice with methylene chloride. The combined organics were dried (Na2SO4), filtered, and concentrated to give 1-(3,5-difluoro-4-hydroxyphenyl)ethanone (10 g, 91%), mp 141-143° C.; MS m/z 171 (M−H).

Workup

  1. temperatureat reflux for 30 h
  2. extractionthe aqueous layer was extracted twice with methylene chloride
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b7f24d533f3446208c74a6c4dcfea0bb
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Reaction notes

Loading…