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

HRID 1156793Notes

Reaction equation

HRID 1156793 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 3.155 g (0.199 m) of o-fluorobenzoyl chloride in 100 ml 1,2-dichloro ethane 26.54 g (0.199 m) of AlCl3 is added over a 30-minute period. The mixture turns yellow then dark. A solution of 32 g (0.181 m) of 2,3-dichloro anisole in 50 ml of 1,2-dichloroethane is added dropwise. There is an evolution of gas and the temperature rises to 35° C. The mixture is stirred 2 hours and then poured over 100 ml concentrated HCl and 100 ml ice. The organic solvent is evaporated in vacuo and the mixture is extracted with ether. The ether extract is washed with 10% K2CO3, washed with water, dried (Na2SO4) and evaporated to give a solid which is recrystallized from ether-hexane giving 38.69 g (70%) of 2'-fluoro-4-methoxy-2,3-dichlorobenzophenone, m.p. 74°-77° C.

Workup

  1. customrises to 35° C
  2. customThe organic solvent is evaporated in vacuo
  3. extractionthe mixture is extracted with ether
  4. extractionThe ether extract
  5. washis washed with 10% K2CO3
  6. washwashed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customto give a solid which
  10. customis recrystallized from ether-hexane giving 38.69 g (70%) of 2'-fluoro-4-methoxy-2,3-dichlorobenzophenone, m.p. 74°-77° C.

Sources & evidence

ORD record
ord-982141c06d6f4200b453280074704665
Source dataset
uspto-grants-1982_06
Patent number
US04337261

Reaction notes

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