Water → 1-(5-Bromo-3-fluoro-2-hydroxyphenyl)ethan-1-one

HRID 38998Notes

Reaction equation

HRID 38998 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].C([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[F:16])(=O)C.O.[CH3:18][CH2:19][O:20]C(C)=O>>[Br:15][C:12]1[CH:11]=[C:10]([F:16])[C:9]([OH:8])=[C:14]([C:19](=[O:20])[CH3:18])[CH:13]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 6451240Aluminum(III) ChlorideHCID 226485254-Bromo-2-fluorophenyl acetate

Product 1

HCID 575158461-(5-Bromo-3-fluoro-2-hydroxyphenyl)ethan-1-one

Conditions

Temperature
150 °C

Procedure

AlCl3 (5.0 g, 38 mmol) was added in portions to 4-bromo-2-fluorophenyl acetate (5.8 g, 25 mmol). The mixture was heated at 150° C. for 3 h and then brought to ambient temperature. Water (ice-cold) was slowly added and then EtOAc. The resulting mixture was vigorously stirred and then the phases were separated and the water phase extracted with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness to give the title compound (5.3 g). MS m/z (rel. intensity, 70 eV) 233 (M+, 55), 232 (M+, 56), 218 (98), 217 (bp), 161 (10).

Workup

  1. custombrought to ambient temperature
  2. customthe phases were separated
  3. extractionthe water phase extracted with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-654553996de24bb3b9c3cb617d7d71f5
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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