Hydrochloric Acid → 2-Chloro-1-(3,4-difluorophenyl)ethanone

HRID 251516

Reaction equation

HRID 251516 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12].[Cl:13][CH2:14][C:15](Cl)=[O:16].Cl>O>[Cl:13][CH2:14][C:15]([C:9]1[CH:10]=[CH:11][C:6]([F:5])=[C:7]([F:12])[CH:8]=1)=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 97061,2-DifluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 23923212-Chloro-1-(3,4-difluorophenyl)ethanoneYield 80.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Aluminium trichloride (210.2 g) was added to 1,2-difluorobenzene (200.0 g) at room temperature. The obtained slurry was heated to 50° C., then chloroacetyl chloride (198.0 g) was added over 50 minutes. The reaction mixture was stirred for an additional 60 minutes, then added slowly to a mixture of ice (786.0 g), water (196.0 g) and 37 wt % hydrochloric acid (297.0 g), during the addition the temperature was kept below 60° C. After the addition, the reaction mixture was heated to 60° C. and the layers separated. The organic layer was washed twice with a 20 w/v % sodium chloride solution (200.0 mL). 2-Chloro-1-(3,4-difluorophenyl)ethanone (270.2 g) was obtained by vacuum distillation of the organic layer.

Workup

  1. customwas kept below 60° C
  2. additionAfter the addition
  3. temperaturethe reaction mixture was heated to 60° C.
  4. customthe layers separated
  5. washThe organic layer was washed twice with a 20 w/v % sodium chloride solution (200.0 mL)

Sources & evidence

ORD record
ord-b7426b474d3f42bd9d4767851118fb29
Source dataset
uspto-grants-2011_01
Patent number
US07863469B2

Linked notes

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