Acetyl chloride → 2'-Fluoro-4'-hydroxyacetophenone

HRID 497212Notes

Reaction equation

HRID 497212 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1.[C:13](Cl)(=[O:15])[CH3:14]>ClCCCl>[F:5][C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][C:11]=1[C:13](=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 97433-FluorophenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27249122'-Fluoro-4'-hydroxyacetophenoneYield 8.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred suspension of aluminum chloride (41.6 g, 312 mmol) in 1,2-dichloroethane (100 ml) was added 3-fluorophenol (30.95 g, 276 mmol) dropwise at 0° C. Acetyl chloride (24.0 g, 306 mmol) was added dropwise, and the mixture was heated at reflux temperature for 6 hours. The mixture was cooled down to room temperature, and poured into ice. The whole was extracted with diethylether. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was recrystallized with hexane to give the title compound (3.57 g, 8% yield). 1H-NMR (CDCl3) δ: 7.88-7.82 (m, 1H), 6.74 (dd, J=92 Hz, 1H), 6.64 (dd, J=13, 2 Hz, 1H), 2.62 (d, J=5 Hz, 3H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 6 hours
  3. additionpoured into ice
  4. extractionThe whole was extracted with diethylether
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized with hexane

Sources & evidence

ORD record
ord-2290fda2378942ea9e3194ed0940cb93
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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