4-Chlorophenol → HCID 21700095, compound

HRID 1978027Notes

Reaction equation

HRID 1978027 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH3:15][S:16]([C:19]1[CH:24]=[CH:23][C:22](F)=[CH:21][CH:20]=1)(=[O:18])=[O:17]>CS(C)=O>[CH3:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 21700095HCID 21700095, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 4-chlorophenol (5.54 g, 43 mmol) in DMSO (75 mL) was treated sequentially with potassium t-butoxide (5.15 g, 46 mmol) then with a solution of 4-fluorophenyl methyl sulfone (5.00 g, 29 mmol) in DMSO (25 mL), heated at 120° C. for 2 hours, cooled to room temperature, then partitioned between dichloromethane and 1 N sodium hydroxide, dried (Mg2SO4), filtered, and concentrated to give crude product as a white solid. Recrystallization from ethyl acetate and hexane afforded 5.44 g (66%) of the desired product.

Workup

  1. custompartitioned between dichloromethane and 1 N sodium hydroxide
  2. dry with materialdried (Mg2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product as a white solid
  6. customRecrystallization from ethyl acetate and hexane

Sources & evidence

ORD record
ord-7963f79206ed47259557d6c587867356
Source dataset
uspto-grants-2001_05
Patent number
US06235786B1

Reaction notes

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