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

HRID 1578860Notes

Reaction equation

HRID 1578860 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:18](Cl)(=[O:20])[CH3:19].Cl>C(=S)=S>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][C:11]([C:18](=[O:20])[CH3:19])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 675792-FluorobiphenylHCID 6451240Aluminum(III) Chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

A solution of 200 g of 2-fluorobiphenyl in 1500 ml of carbon disulfide was cooled to 0°-5°C and successively treated with 200 g of aluminum chloride over a period of 140 minutes and 113 g of acetyl chloride over a period of 165 minutes. The resulting mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture then was poured carefully into a mixture of ice and aqueous hydrochloric acid. Organic materials were extracted from the resulting acidic mixture with a mixture of diethyl ether and ethyl acetate. The organic extract was washed successively with water, ten percent aqueous sodium hydroxide, and water, and dried over anhydrous sodium sulfate. The solvents were evaporated under reduced pressure and the solid residue was recrystallized from hexane to give 4'-(2-fluorophenyl)acetophenone. Recrystallization of the material from hexane gave two crops of crystals having the following elemental analyses:

Workup

  1. extractionOrganic materials were extracted from the resulting acidic mixture with a mixture of diethyl ether and ethyl acetate
  2. extractionThe organic extract
  3. washwas washed successively with water, ten percent aqueous sodium hydroxide, and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvents were evaporated under reduced pressure
  6. customthe solid residue was recrystallized from hexane

Sources & evidence

ORD record
ord-6d56040ab27a466eb9617119b288e079
Source dataset
uspto-grants-1976_02
Patent number
US03939278

Reaction notes

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