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

HRID 1155408Notes

Reaction equation

HRID 1155408 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 CS2 was cooled to 0°-5° C. and treated with 200 g. of aluminum chloride over 140 minutes and then with 113 g. of acetyl chloride over 165 minutes. The mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was then poured carefully into ice and hydrochloric acid, and organic material was extracted with a mixture of diethyl ether and ethyl acetate. The organic extract was washed with water, 10% sodium hydroxide, and water, and dried over sodium sulfate. Evaporation of the solvents in vacuo and recrystallization of the solid residue from hexane gave (4'-(2-fluorophenyl)acetophenone. This was recrystallized from hexane to give two crops Crop one, 173 g., m.p. 84.5°-86.5° C.

Workup

  1. additiontreated with 200 g
  2. extractionwas extracted with a mixture of diethyl ether and ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water, 10% sodium hydroxide, and water
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvents
  7. customin vacuo and recrystallization of the solid residue from hexane

Sources & evidence

ORD record
ord-b65b30a136ad4ac6bd69093dee8f7fa4
Source dataset
uspto-grants-1981_11
Patent number
US04301313

Reaction notes

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