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

HRID 2274113Notes

Reaction equation

HRID 2274113 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[C:10](Cl)(=[O:12])[CH3:11].[Cl-].[Cl-].[Cl-].[Al+3]>>[Cl:1][C:2]1[C:3]([F:9])=[CH:4][C:5]([OH:8])=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=1

Participants

4

Reactant 3

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

Product 1

HCID 162214361-(5-Chloro-4-fluoro-2-hydroxyphenyl)ethanone

Conditions

Temperature
60 °C

Procedure

To 4-chloro-3-fluorophenol (Oakwood #004459, 5.1 g, 35 mmol) was added acetyl chloride (3.6 mL, 51 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 reaction mixture was then cooled to room temperature and slowly quenched with 1M HCl while cooling in an ice-bath and stirred for 30 minutes. The precipitate was washed well with water and dried under vacuum to give the desired product (quantitative). This material was used without further purification. 1H NMR (300 MHz, CDCl3): δ 12.41 (s, 1H), 7.80 (m, 1H), 6.79 (m, 1H), 2.60 (s, 3H).

Workup

  1. temperaturethe mixture was heated at 180° C. for 30 minutes
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customslowly quenched with 1M HCl
  4. temperaturewhile cooling in an ice-bath
  5. washThe precipitate was washed well with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b94f22a35f924bd18abc3e0fcee15031
Source dataset
uspto-grants-2015_09
Patent number
US09126948B2

Reaction notes

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