Dichloromethane → 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]ethan-1-one

HRID 1598505Notes

Reaction equation

HRID 1598505 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[CH:6]=[C:7]([C:15]([F:18])([F:17])[F:16])[CH:8]=[C:9]([Cl:14])[C:10]=1[CH:11]([OH:13])[CH3:12].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>CCOCC>[C:11]([C:10]1[C:9]([Cl:14])=[CH:8][C:7]([C:15]([F:18])([F:16])[F:17])=[CH:6][C:5]=1[Cl:4])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 18929411HCID 18929411, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 27368641-[2,6-Dichloro-4-(trifluoromethyl)phenyl]ethan-1-oneYield 80.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An anhydrous methylene chloride solution (50 ml) of 23.5 g of 3,5-dichloro-4-(1-hydroxyethyl)benzotrifluoride (9) was added at a time to 100 ml of an anhydrous methylene chloride suspension of 30.0 g of pyridinium chlorochromate and 20 g of Celite at room temperature, and the mixture was stirred overnight. The reaction mixture was diluted with 100 ml of ether and thereafter applied to a column packed with 100 g of silica gel. Ether was used for elution, and the eluent was concentrated under reduced pressure to obtain 18.7 g of the desired compound in the form of a yellow oil (crude yield 72.8%).

Workup

  1. washEther was used for elution
  2. concentrationthe eluent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8b2d9981ee074e97905bd00028ae7039
Source dataset
uspto-grants-1998_04
Patent number
US05739083

Reaction notes

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