2-Fluorobenzoyl chloride → 2,3-Dichloro-4-(2-fluorobenzoyl)phenetole

HRID 1263290Notes

Reaction equation

HRID 1263290 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH2:10][CH3:11].[F:12][C:13]1[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:15](=[O:16])[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[F:12])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 98082-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 104200611,2-Dichloro-3-ethoxybenzene

Product 1

HCID 133437072,3-Dichloro-4-(2-fluorobenzoyl)phenetoleYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,3-dichlorophenetole (57.3 g., 0.3 mole), 2-fluorobenzoyl chloride (47.8 g., 0.3 mole) and methylene chloride (300 ml.) at 5° C. was stirred vigorously and treated with finely powdered aluminum chloride (42.6 g., 0.32 ml.). The reaction mixture was slowly warmed to room temperature and then stirred overnight. The reaction mixture was decomposed with ice/concentrated hydrochloric acid (50 ml.) and the aqueous solution was extracted twice with methylene chloride. The combined organic extracts were washed with aqueous sodium bicarbonate solution and finally with aqueous sodium chloride solution. The methylene chloride solution was dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue on triturating with methanol gave the product 55 g., m.p. 94°-95° C. This material was used in the next step without additional purification.

Workup

  1. stirringstirred overnight
  2. extractionthe aqueous solution was extracted twice with methylene chloride
  3. washThe combined organic extracts were washed with aqueous sodium bicarbonate solution and finally with aqueous sodium chloride solution
  4. dry with materialThe methylene chloride solution was dried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customthe residue on triturating with methanol

Sources & evidence

ORD record
ord-b4b20749a6234ccdac3f6a207c478372
Source dataset
uspto-grants-1984_06
Patent number
US04456612

Reaction notes

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