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

HRID 2042602Notes

Reaction equation

HRID 2042602 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-56e9bcb5a54948468a7c9ffea9046235
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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