Water → 3-Chloro-2'-fluoro-2-hydroxy-4-methoxybenzophenone

HRID 568666Notes

Reaction equation

HRID 568666 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[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16].[Al+3].[Cl-].[Cl-].[Cl-].O>ClC(Cl)C>[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]=[CH:21][C:13]=1[F:12])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 98082-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 130157172-Chloro-1,3-dimethoxybenzene

Product 1

HCID 130157183-Chloro-2'-fluoro-2-hydroxy-4-methoxybenzophenone

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-chlororesorcinol dimethyl ether (22.0 g) and o-fluorobenzoyl chloride (20.2 g) are dissolved in 250 ml of dichloroethane, chilled in an ice bath and treated with AlCl3 (18.6 g). Fifteen minutes after the addition is complete, the reaction is heated to reflux for 30 minutes. It is poured into H2O and extracted with ethylacetate. Evaporation and trituration with hexane gives 3-chloro-2'-fluoro-2-hydroxy-4-methoxybenzophenone, mp 132°-133° C.

Workup

  1. temperaturechilled in an ice bath
  2. additionFifteen minutes after the addition
  3. temperaturethe reaction is heated
  4. temperatureto reflux for 30 minutes
  5. extractionextracted with ethylacetate
  6. customEvaporation and trituration with hexane

Sources & evidence

ORD record
ord-e22f11222ac44074a7fb3bca009e012a
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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