2,3-Difluorobenzoyl chloride → 3-Chloro-2-hydroxy-4-methoxy-2',3'-difluorobenzophenone

HRID 568660Notes

Reaction equation

HRID 568660 reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:5]([O:6][CH3:7])[C:4]=1[Cl:11].[F:12][C:13]1[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[Cl:11][C:4]1[C:3]([OH:2])=[C:10]([CH:9]=[CH:8][C:5]=1[O:6][CH3:7])[C:15]([C:14]1[CH:18]=[CH:19][CH:20]=[C:21]([F:22])[C:13]=1[F:12])=[O:16]

Participants

5

Reactant 3

HCID 5195492,3-Difluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 130157172-Chloro-1,3-dimethoxybenzene

Product 1

HCID 140125643-Chloro-2-hydroxy-4-methoxy-2',3'-difluorobenzophenone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 4 g of 2-chlororesorcinol dimethyl ether and 3.7 g of 2,3-difluorobenzoyl chloride in 60 ml of 1,2-dichloroethane at 5° C., 3.06 g of AlCl3 is added in portions. The mixture is allowed to warm to room temperature and then refluxed for 30 minutes. The reaction mixture is poured into concentrated HCl-ice and is permitted to stand about 72 hours. The aqueous layer is extracted with additional organic solvent, dried over Na2SO4 and evaporated to give 3-chloro-2-hydroxy-4-methoxy-2',3'-difluorobenzophenone, mp 161°-162° C.

Workup

  1. temperaturerefluxed for 30 minutes
  2. extractionThe aqueous layer is extracted with additional organic solvent
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-66c469047c4a4f25af070c9e085e2bb8
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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