Hydrochloric Acid → 3'-Chloro-4'-fluoroacetophenone

HRID 635542

Reaction equation

HRID 635542 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5](Cl)=[O:6].Cl[C:13]1C=CC=CC=1F.C(Cl)(=O)C.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClC(Cl)=C(Cl)Cl.C(Cl)Cl.C(=S)=S>[CH3:13][C:5]([C:4]1[CH:8]=[CH:9][C:10]([F:11])=[C:2]([Cl:1])[CH:3]=1)=[O:6]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 95831-Chloro-2-fluorobenzeneHCID 27365483-Chloro-4-fluorobenzoyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5204223'-Chloro-4'-fluoroacetophenoneYield 80%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6348Carbon DisulfideSolventHCID 31373TetrachloroethyleneSolvent

Procedure

3-Chloro-4-fluorobenzoyl chloride is available via a multi-stage synthesis. According to Diep et al., J. Chem. Soc. [1963], 2784-2787, ortho-chlorofluorobenzene is initially reacted with acetyl chloride in the presence of large amounts of aluminum chloride in the presence of carbon disulfide, methylene chloride or tetrachloroethylene, the reaction mixture is decomposed with dilute hydrochloric acid, the organic phase is washed with aqueous sodium hydroxide, then with water, and dried over sodium sulfate, the solvent is evaporated, and the residue is subjected to fractional distillation at reduced pressure. This method gives 3-chloro-4-fluoroacetophenone in a yield of about 80%.

Workup

  1. washthe organic phase is washed with aqueous sodium hydroxide
  2. dry with materialwith water, and dried over sodium sulfate
  3. customthe solvent is evaporated
  4. distillationthe residue is subjected to fractional distillation at reduced pressure

Sources & evidence

ORD record
ord-f9495f7508b342e992643886567fff12
Source dataset
uspto-grants-2001_02
Patent number
US06187952B1

Linked notes

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