Acetyl chloride → 1-(5-Chloro-4-fluoro-2-hydroxyphenyl)ethanone

HRID 510997Notes

Reaction equation

HRID 510997 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[F:13].[Cl-].[Cl-].[Cl-].[Al+3]>Cl>[Cl:5][C:6]1[C:7]([F:13])=[CH:2][C:1]([OH:3])=[C:10]([C:9](=[O:12])[CH3:8])[CH:11]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 27245234-Chloro-3-fluorophenolHCID 6451240Aluminum(III) Chloride

Product 1

HCID 162214361-(5-Chloro-4-fluoro-2-hydroxyphenyl)ethanoneYield 100%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
60 °C

Procedure

Acetyl chloride (3.6 mL, 51 mmol) was added to 4-chloro-3-fluorophenol (5.1 g, 35 mmol) and the resulting mixture was heated at 60° C. for 2 hours. Aluminum trichloride (7.0 g, 52 mmol) was added and the mixture was heated at 180° C. for 30 minutes. The mixture was cooled to room temperature. The mixture was cooled to 0° C. and 1 N HCl solution (100 mL) was added dropwise over 30 minutes. The precipitate was washed well with water and dried under vacuum to give the desired compound (6.6 g, 100%).

Workup

  1. temperaturethe mixture was heated at 180° C. for 30 minutes
  2. temperatureThe mixture was cooled to room temperature
  3. temperatureThe mixture was cooled to 0° C.
  4. washThe precipitate was washed well with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-2f6414cfd1f04e0396a7005ee86b48e4
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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