Hydrochloric Acid → 2,3-Dichloro-4-methoxy-4'-chloro-2'-fluorobenzophenone

HRID 568691Notes

Reaction equation

HRID 568691 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([F:11])[CH:3]=1.[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[O:20][CH3:21].[Al+3].[Cl-].[Cl-].[Cl-].Cl>ClCCCl>[Cl:19][C:18]1[C:13]([Cl:12])=[C:14]([O:20][CH3:21])[CH:15]=[CH:16][C:17]=1[C:6]([C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=1[F:11])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 161262,3-DichloroanisoleHCID 27736014-Chloro-2-fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 140972672,3-Dichloro-4-methoxy-4'-chloro-2'-fluorobenzophenone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 46 g of 4-chloro-2-fluorobenzoyl chloride and 38.9 g of 2,3-dichloroanisole in 150 ml of 1,2-dichloroethane, 32 g of AlCl3 is added gradually. The mixture is warmed to 40° C. with a vigorous evolution of gas. The mixture is poured into concentrated HCl and ice. The organic layer is separated and the aqueous layer is extracted with additional organic solvent. The combined organic extracts are washed with water, dried over Na2SO4 and evaporated. The crude product is triturated with hexane to give 2,3-dichloro-4-methoxy-4'-chloro-2'-fluorobenzophenone. An analytical sample is recrystallized from EtOH, mp 115°-116° C.

Workup

  1. additionis added gradually
  2. customThe organic layer is separated
  3. extractionthe aqueous layer is extracted with additional organic solvent
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe crude product is triturated with hexane

Sources & evidence

ORD record
ord-bc590864a6fc47a98ea3d7f652422ddd
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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