Cesium carbonate → Methyl 5-methanesulfonyl-2-methyl-4-(3-pentafluorosulfanylphenoxy)benzoate

HRID 269416Notes

Reaction equation

HRID 269416 reaction equation
F[C:2]1[C:11]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:16])[CH:3]=1.[F:17][S:18]([F:29])([F:28])([F:27])([F:26])[C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CC(=O)OCC>[CH3:15][S:12]([C:11]1[C:2]([O:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([S:18]([F:29])([F:17])([F:26])([F:27])[F:28])[CH:20]=2)=[CH:3][C:4]([CH3:16])=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:14])=[O:13]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27792013-(Pentafluorothio)phenolHCID 10538364Methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate

Product 1

HCID 11704977Methyl 5-methanesulfonyl-2-methyl-4-(3-pentafluorosulfanylphenoxy)benzoateYield 27.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

600 mg of methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate, 700 mg of 3-pentafluorosulfanylphenol and 1.6 g of Cs2CO3 were stirred in 4 ml of anhydrous DMF at 100° C. for 3 h. The mixture was then cooled to RT, diluted with 100 ml of EA and washed 3 times with 20 ml of water each time. The residue after drying over MgSO4 and removal of the solvent in vacuo was chromatographed on silica gel with DIP. 300 mg of a colorless oil were obtained.

Workup

  1. washwashed 3 times with 20 ml of water each time
  2. dry with materialThe residue after drying over MgSO4 and removal of the solvent in vacuo
  3. customwas chromatographed on silica gel with DIP

Sources & evidence

ORD record
ord-e496ae035748440380b7ce3aea1afcba
Source dataset
uspto-grants-2008_11
Patent number
US07446225B2

Reaction notes

Loading…