4-Fluorophenol → 4-Fluorophenyl 2-chlorobenzoate

HRID 1871810Notes

Reaction equation

HRID 1871810 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([O:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:13]

Participants

5

Reactant 2

HCID 97324-FluorophenolHCID 691102-Chlorobenzoyl chloride

Product 1

HCID 27982194-Fluorophenyl 2-chlorobenzoateYield 87.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

To a stirred solution of 25 g of 4fluorophenol in 40 cc of pyridine and 30 cc of toluene was added dropwise 40.9 g of 2-chlorobenzoylchloride at room temperature. And the resulting mixture was stirred at room temperature for 16 hours. Ice water was added to the reaction mixture and extracted with ethyl acetate. The ethylacetate layer was washed 4 times with 1N HCl, dried over magnesium sulfate. The solvent was distilled off and the crude product thus obtained was recrystallized from hexane to obtain 49.1 g of compound A. Yield: 87.8%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethylacetate layer was washed 4 times with 1N HCl
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe crude product thus obtained
  6. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-75da8e8575ea426abfb122840248e2d7
Source dataset
uspto-grants-2000_08
Patent number
USRE036832

Reaction notes

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