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

HRID 887031Notes

Reaction equation

HRID 887031 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-ebba247cacdc419cac68509994e37e2e
Source dataset
uspto-grants-2012_08
Patent number
US08247414B2

Reaction notes

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