Hydrochloric Acid → 2,3-Dichloro-4-methoxy-2',6'-difluorobenzophenone

HRID 568621Notes

Reaction equation

HRID 568621 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[Al+3].[Cl-].[Cl-].[Cl-].[Cl:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[O:24][CH3:25].Cl>ClCCCl>[Cl:23][C:22]1[C:17]([Cl:16])=[C:18]([O:24][CH3:25])[CH:19]=[CH:20][C:21]=1[C:4]([C:3]1[C:2]([F:1])=[CH:10][CH:9]=[CH:8][C:7]=1[F:11])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 161262,3-DichloroanisoleHCID 874382,6-Difluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 140125532,3-Dichloro-4-methoxy-2',6'-difluorobenzophenone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 24.6 g of 2,6-difluoro benzoylchloride in 100 ml of 1,2-dichloroethane, 18.5 g of AlCl3 is added in portions over a 30 minute period. A solution of 22.5 g of 2,3-dichloroanisole in 100 ml of 1,2-dichloroethane is added thereto. The mixture is stirred for one hour and poured over 100 ml concentrated HCl and ice. The organic layer is separated and the aqueous layer extracted with CHCl3. The organic extract is washed with water, dried (Na2SO4) and evaporated to give an oil which crystallizes from hexane to yield solid 2,3-dichloro-4-methoxy-2',6'-difluorobenzophenone which upon recrystallization from ether has an mp 94°-96° C.

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer extracted with CHCl3
  3. extractionThe organic extract
  4. washis washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give an oil which
  8. customcrystallizes from hexane

Sources & evidence

ORD record
ord-5e91dbb065f5441eb65271162dd3fe07
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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