Hydrochloric Acid → (2,4-Dimethyl-phenyl)-(4-fluoro-phenyl)-methanone

HRID 990279

Reaction equation

HRID 990279 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.Cl.[C:16]1([CH3:23])[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=1>>[CH3:23][C:16]1[CH:21]=[CH:20][C:19]([C:10](=[O:11])[C:9]2[CH:13]=[CH:14][C:6]([F:5])=[CH:7][CH:8]=2)=[C:18]([CH3:22])[CH:17]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7929M-XyleneHCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10242880(2,4-Dimethyl-phenyl)-(4-fluoro-phenyl)-methanoneYield 99%

Conditions

Temperature
5 °C

Procedure

To a suspension of anhydrous aluminum chloride (19.5 g) dispersed in m-xylene (150 ml) was added dropwise 4-fluorobenzoyl chloride (21.1 g) under ice-cooling. The mixture was stirred at 0-10° C. for 3 hr and poured into 6N hydrochloric acid. The reaction mixture was partitioned and the obtained organic layer was washed successively with water, 10% aqueous sodium hydroxide solution and water. The solvent was evaporated to give a 96:4 mixture (30.2 g, 99%) of 1,3-dimethyl-4-(4′-fluorobenzoyl)benzene and 1,3-dimethyl-2-(4′-fluorobenzoyl)benzene as pale-yellow oil.

Workup

  1. temperaturecooling
  2. customThe reaction mixture was partitioned
  3. washthe obtained organic layer was washed successively with water, 10% aqueous sodium hydroxide solution and water
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ff422259f12942c5b7045da236965ede
Source dataset
uspto-grants-2002_10
Patent number
US06458975B1

Linked notes

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