4-Fluorophenol → HCID 86590253, compound

HRID 1677858Notes

Reaction equation

HRID 1677858 reaction equation
Cl[C:2]1[CH:11]=[C:10]([S:12]([F:17])([F:16])([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CC(=O)OCC>[F:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:2]2[CH:11]=[C:10]([S:12]([F:17])([F:16])([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 86622591HCID 86622591, compound

Product 1

HCID 86590253HCID 86590253, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

300 mg of methyl 2-chloro-4-pentafluorosulfanylbenzoate, 113 mg of 4-fluorophenol and 659 mg of Cs2CO3 were dissolved in 1.5 ml of DMF (anhydrous) and stirred at 120° C. The mixture was then allowed to cool and was diluted with 10 ml of EA and washed 3 times with 5 ml of water each time. Drying over MgSO4 was followed by removal of the solvent in vacuo. 120 mg of an amorphous solid were obtained and were chromatographed on reversed phase silica gel:

Workup

  1. temperatureto cool
  2. washwashed 3 times with 5 ml of water each time
  3. dry with materialDrying over MgSO4
  4. customwas followed by removal of the solvent in vacuo

Sources & evidence

ORD record
ord-6c197eb516184e81aa25b6f4f2b786be
Source dataset
uspto-grants-2011_08
Patent number
US08008352B2

Reaction notes

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