Hydrochloric Acid → 3-Chloro-2',5'-difluoro-2-hydroxy-4-methoxybenzophenone

HRID 568669Notes

Reaction equation

HRID 568669 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:16]([O:17]C)[C:15]=1[Cl:22].[Al+3].[Cl-].[Cl-].[Cl-].Cl>ClCCCl>[Cl:22][C:15]1[C:16]([OH:17])=[C:19]([CH:20]=[CH:21][C:14]=1[O:13][CH3:12])[C:4]([C:3]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:2]=1[F:1])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5880822,5-Difluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 130157172-Chloro-1,3-dimethoxybenzene

Product 1

HCID 140125663-Chloro-2',5'-difluoro-2-hydroxy-4-methoxybenzophenone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 21 g of 2,5-difluorobenzoyl chloride and 20.4 g of 2-chlororesorcinol dimethyl ether in 250 ml of 1,2-dichloroethane at 5°-10° C. 15.7 g of AlCl3 is added in portions. The mixture is allowed to warm to room temperature and is then refluxed for 30 minutes. The mixture is poured into concentrated HCl and ice and stirred for approximately one hour. The product is extracted with ethyl acetate, dried over Na2SO4 and evaporated to give 3-chloro-2',5'-difluoro-2-hydroxy-4-methoxybenzophenone, mp 178°-180° C.

Workup

  1. temperatureis then refluxed for 30 minutes
  2. extractionThe product is extracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-c690c6026fd240e885713eef96363648
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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