Acetic Anhydride → Acetophenone, 2',4'-dichloro-5'-fluoro-

HRID 47875

Reaction equation

HRID 47875 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>[CH3:15][C:14]([C:7]1[C:2]([Cl:1])=[CH:3][C:4]([Cl:9])=[C:5]([F:8])[CH:6]=1)=[O:16]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 123112Benzene, 2,4-dichloro-1-fluoro-HCID 6451240Aluminum(III) Chloride2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a warm solution of 1,3-dichloro4-fluorobenzene at 70° C. (175.0 gm), anhydrous aluminum chloride was added in small portion with stirring (260.0 g). Then acetic anhydride was added in small portion with stirring (125 mL) followed by an additional amount of aluminum chloride (159.0 g). The temperature was slowly raised to 120° C. with stirring for 25 hours. The thick reaction mixture was cooled and poured into 400 cc of concentrated hydrochloric acid containing ice. The oil was extracted with methylene chloride, washed with water, dried over anhydrous magnesium sulfate and concentrated to give 165.0 g of oil (2).

Workup

  1. stirringwith stirring (125 mL)
  2. stirringwith stirring for 25 hours
  3. temperatureThe thick reaction mixture was cooled
  4. additioncontaining ice
  5. extractionThe oil was extracted with methylene chloride
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cebb852cfbc54d24ad1af9351ccb2ecd
Source dataset
uspto-grants-2004_03
Patent number
US06699989B1

Linked notes

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