Hydrochloric Acid → Acetophenone, 2',4'-dichloro-5'-fluoro-

HRID 2165648Notes

Reaction equation

HRID 2165648 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([Cl:9])[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:14](OC(=O)C)(=[O:16])[CH3:15].Cl>>[C:14]([C:7]1[C:2]([Cl:1])=[CH:3][C:4]([Cl:9])=[C:5]([F:8])[CH:6]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 123112Benzene, 2,4-dichloro-1-fluoro-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 727250Acetophenone, 2',4'-dichloro-5'-fluoro-

Conditions

Temperature
80 °C

Procedure

A mixture of 229.6 g of 1,3-dichloro-4-fluorobenzene and 205.34 g of aluminum chloride was heated at 80° C. A 56 g portion of acetic anhydride was added dropwise over 2 hours, then the reaction was heated at 100° C. for 8 hours, poured onto a mixture of concentrated hydrochloric acid and ice and extracted several times with ether. The ether extracts were combined, washed with water, dried and the solvents evaporated. The solid was purified by vacuum distillation, giving 156.63 g of 6-acetyl-1,3-dichloro-4-fluorobenzene.

Workup

  1. temperaturethe reaction was heated at 100° C. for 8 hours
  2. extractionextracted several times with ether
  3. washwashed with water
  4. customdried
  5. customthe solvents evaporated
  6. distillationThe solid was purified by vacuum distillation

Sources & evidence

ORD record
ord-59c5a5f9dc434f8d9cba145093dabb13
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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