3,4-Dichlorophenol → 4-Methylphenyl 5-chloro-4-(3,4-dichlorophenoxy)-2-fluorobenzoate

HRID 2359279Notes

Reaction equation

HRID 2359279 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[C:18](F)=[CH:19][C:20]([F:33])=[C:21]([CH:32]=1)[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)=[O:23]>CS(C)=O.C(OCC)(=O)C>[Cl:16][C:17]1[C:18]([O:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)=[CH:19][C:20]([F:33])=[C:21]([CH:32]=1)[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)=[O:23]

Participants

6

Reactant 3

HCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 58042518HCID 58042518, compound

Product 1

HCID 580463024-Methylphenyl 5-chloro-4-(3,4-dichlorophenoxy)-2-fluorobenzoateYield 100.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,4-Dichlorophenol (110 mg, 0.67 mmol) and potassium carbonate (20 mg, 1.42 mmol) were stirred in dimethylsulfoxide (20 mL). After 5 minutes, 4-methylphenyl 5-chloro-2,4-difluorobenzoate (Preparation 10, 200 mg, 0.71 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with a 1M aqueous solution of sodium hydroxide. The aqueous phase was extracted with ethyl acetate. The combined organic phase was dried over magnesium sulphate, filtered and concentrated in vacuo to give a white solid. The solid was purified by silica gel column chromatography (50% ethyl acetate in heptane elution) to afford the title compound as a white solid (286 mg, 95%).

Workup

  1. washwashed with a 1M aqueous solution of sodium hydroxide
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialThe combined organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a white solid
  7. customThe solid was purified by silica gel column chromatography (50% ethyl acetate in heptane elution)

Sources & evidence

ORD record
ord-112a8016cea34f3caff23e7fa4339a30
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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