4-Chlorophenol → Methyl 5-bromo-4-(4-chlorophenoxy)-2-fluorobenzoate

HRID 1620346Notes

Reaction equation

HRID 1620346 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Br:9][C:10]1[C:11](F)=[CH:12][C:13]([F:20])=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[Br:9][C:10]1[C:11]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:12][C:13]([F:20])=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 18007754Methyl 5-bromo-2,4-difluorobenzoate

Product 1

HCID 66666677Methyl 5-bromo-4-(4-chlorophenoxy)-2-fluorobenzoateYield 83%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 4-chlorophenol (94.7 mg, 0.74 mmol), methyl 5-bromo-2,4-difluorobenzoate (Preparation 18, 168 mg, 0.67 mmol), and potassium carbonate (277 mg, 2.01 mmol) in dimethyl sulfoxide (3 mL) was stirred for 16 hours at room temperature under a nitrogen atmosphere. The reaction was diluted with water (30 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were successively washed with aqueous sodium hydroxide solution (1.0 M, 20 mL), brine (2×30 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a colourless oil (199 mg, 83%).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined organic extracts were successively washed with aqueous sodium hydroxide solution (1.0 M, 20 mL), brine (2×30 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54b682792f114a4ebf9134ca0c83b472
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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