Water → 1-(2'-Fluoro[1,1'-biphenyl]-4-yl)ethanone

HRID 1870837Notes

Reaction equation

HRID 1870837 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:18](Cl)(=[O:20])[CH3:19].O>C(Cl)Cl>[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:13]=[CH:14][C:15]([C:18](=[O:20])[CH3:19])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 675792-FluorobiphenylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 676621-(2'-Fluoro[1,1'-biphenyl]-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere, methylene chloride (100 ml) was added to aluminum chloride (20.1 g) and then, to thereto was added dropwise at room temperature a solution obtained by dissolving 2-fluorobiphenyl (20.0 g) and acetyl chloride (10.7 ml) in methylene chloride (100 ml). After stirring for 4 hours, a small amount of water was added to the reaction mixture, and then the mixture was subjected to extraction with chloroform. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The residue was purified by a recrystallization method from ethanol, to obtain 1-(2'-fluoro-biphenyl-4-yl)-ethanone (17.53 g).

Workup

  1. additionto thereto was added dropwise at room temperature a solution
  2. customobtained
  3. extractionthe mixture was subjected to extraction with chloroform
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a recrystallization method from ethanol

Sources & evidence

ORD record
ord-dd75456715c14823a4c7a6c8f8ce6181
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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