Sodium Carbonate → Methyl 2-methanesulfonyl-5-methyl-4'-pentafluorosulfanylbiphenyl-4-carboxylate

HRID 130630Notes

Reaction equation

HRID 130630 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].Br[C:38]1[C:47]([S:48]([CH3:51])(=[O:50])=[O:49])=[CH:46][C:41]([C:42]([O:44][CH3:45])=[O:43])=[C:40]([CH3:52])[CH:39]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CC(=O)OCC.O>[CH3:51][S:48]([C:47]1[CH:46]=[C:41]([C:42]([O:44][CH3:45])=[O:43])[C:40]([CH3:52])=[CH:39][C:38]=1[C:2]1[CH:7]=[CH:6][C:5]([S:8]([F:13])([F:12])([F:11])([F:10])[F:9])=[CH:4][CH:3]=1)(=[O:49])=[O:50]

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 27791941-Bromo-4-(pentafluoro-lambda6-sulfanyl)benzeneHCID 10590825Methyl 4-bromo-5-methanesulfonyl-2-methylbenzoate

Product 1

HCID 59731052Methyl 2-methanesulfonyl-5-methyl-4'-pentafluorosulfanylbiphenyl-4-carboxylateYield 65.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

150 mg of 1-bromo-4-pentafluorosulfanylbenzene were stirred together with 135 mg of bis(pinacolato)diboron, 156 mg of potassium acetate and 64 mg of Pd(dppf)2 in 4 ml of DMF at 80° C. for 2 h. Then 163 mg of methyl 4-bromo-5-methanesulfonyl-2-methylbenzoate, 337 mg of Na2CO3, 64 mg of Pd(dppf)2 and 2 ml of water were added, and stirring was continued at 80° C. for 3 h. Cooling was followed by dilution with 50 ml of EA and washing twice with 10 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. 150 mg of a colorless oil were obtained.

Workup

  1. temperatureCooling
  2. washwashing twice with 10 ml of water each time
  3. dry with materialThe residue after drying over MgSO4 and removal of the solvent in vacuo
  4. customwas chromatographed on silica gel with DIP

Sources & evidence

ORD record
ord-7412e31690764de39bd04a555a13186b
Source dataset
uspto-grants-2008_06
Patent number
US07381841B2

Reaction notes

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