Hydrochloric Acid → (2,3-Dichloro-4-methoxyphenyl)(2-fluorophenyl)methanone

HRID 1607892Notes

Reaction equation

HRID 1607892 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Al+3].[Cl-].[Cl-].[Cl-].[Cl:15][C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[O:23][CH3:24].Cl>ClCCCl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](=[O:5])[C:20]1[CH:19]=[CH:18][C:17]([O:23][CH3:24])=[C:16]([Cl:15])[C:21]=1[Cl:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 98082-Fluorobenzoyl chlorideHCID 161262,3-DichloroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13015710(2,3-Dichloro-4-methoxyphenyl)(2-fluorophenyl)methanone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 31.55 g of o-fluorobenzoyl chloride in 100 ml 1,2-dichloroethane, 26.54 g of AlCl3 was added over a 30 minute period. A solution of 32 g of 2,3-dichloroanisole in 50 ml of 1,2-dichloroethane was added dropwise. There was an evolution of gas and the temperature rose to 35°. The mixture was stirred 2 hours and then poured overa mixture of 100 ml concentrated HCl and 100 ml ice. The organic solvent was evaporated in vacuo and the mixture extracted with ether. The ether extract was washed with 10% K2CO3, washed withwater, and dried over Na2SO4, and the ether was evaporated to give a solid. Recrystallization of the solid from the ether-hexane mixturegave 38.69 g (70%) of 2'-fluoro-4-methoxy-2,3-dichlorobenzophenone, m.p. 74°-77°.

Workup

  1. customrose to 35°
  2. additionpoured
  3. customThe organic solvent was evaporated in vacuo
  4. extractionthe mixture extracted with ether
  5. extractionThe ether extract
  6. washwas washed with 10% K2CO3
  7. washwashed withwater, and
  8. dry with materialdried over Na2SO4
  9. customthe ether was evaporated
  10. customto give a solid
  11. customRecrystallization of the solid from the ether-hexane mixturegave 38.69 g (70%) of 2'-fluoro-4-methoxy-2,3-dichlorobenzophenone, m.p. 74°-77°

Sources & evidence

ORD record
ord-078dcfdf00844dd5ac303bcf88d0a659
Source dataset
uspto-grants-1989_09
Patent number
US04868188

Reaction notes

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