Hydrochloric Acid → 2-Chloro-4,6-dimethoxy-2'-fluorobenzophenone

HRID 652911Notes

Reaction equation

HRID 652911 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[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[CH:17]=1.Cl>ClCCl>[Cl:15][C:16]1[CH:17]=[C:18]([O:24][CH3:25])[CH:19]=[C:20]([O:22][CH3:23])[C:21]=1[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[F:1])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 98082-Fluorobenzoyl chlorideHCID 815021-Chloro-3,5-dimethoxybenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 140125692-Chloro-4,6-dimethoxy-2'-fluorobenzophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of o-fluorobenzoyl chloride (47.6 g) in 100 ml dichloromethane is added AlCl3 (40.0 g) portionwise, in about thirty minutes. To this resultant dark solution is added dropwise a solution of 1-chloro-3,5-dimethoxybenzene (52.0 g) in 120 ml dichloromethane, in fifteen minutes. After stirring at ambient temperature for four hours, the mixture is poured into one liter iced-dilute HCl solution and then stirred for 30 minutes. The organic layer is collected, evaporated to an oil, which is dissolved into ether, washed with water, dilute NaOH solution, water, then dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvent is evaporated to a solid, which is purified by silica gel, eluted with dichloromethane to yield 2-chloro-4,6-dimethoxy-2'-fluorobenzophenone, mp 88°-92° C.

Workup

  1. waitin about thirty minutes
  2. waitin fifteen minutes
  3. stirringstirred for 30 minutes
  4. customThe organic layer is collected
  5. customevaporated to an oil, which
  6. dissolutionis dissolved into ether
  7. washwashed with water, dilute NaOH solution, water
  8. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  9. filtrationAfter filtering
  10. customthe solvent is evaporated to a solid, which
  11. customis purified by silica gel
  12. washeluted with dichloromethane

Sources & evidence

ORD record
ord-c6056924bb9a4e1aa42dbaab72414f1d
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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