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

HRID 652920

Reaction equation

HRID 652920 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-065ee68acb964175a273abc4b4654929
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Linked notes

Loading…