Cesium fluoride → HCID 58521957, compound

HRID 2390260Notes

Reaction equation

HRID 2390260 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[F-].[Cs+]>CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:3]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 58521981HCID 58521981, compound2×

Product 1

HCID 58521957HCID 58521957, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-bromo-1-iodo-2-(methylsulfonyl)benzene (Intermediate 202; 200 mg; 0.55 mmol), phenylboronic acid (68 mg; 0.55 mmol;) was placed in a microwave vial and treated with caesium fluoride (252 mg; 1.66 mmol) and bis(triphenylphosphine)palladium(II) chloride (39 mg; 0.06 mmol). The tube was sealed and degased with N2 before adding dioxane (3 ml) and water (1.5 ml). The resulting reaction mixture was irradiated in a microwave reactor at 110° C. for 20 minutes. The reaction mixture was taken up in EtOAc and washed with water and brine. The organic phase was dried over MgSO4, filtered, concentrated and purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc affording the title compound as an orange sticky solid.

Workup

  1. customThe tube was sealed
  2. customdegased with N2
  3. additionbefore adding dioxane (3 ml) and water (1.5 ml)
  4. customThe resulting reaction mixture
  5. customwas irradiated in a microwave reactor at 110° C. for 20 minutes
  6. washwashed with water and brine
  7. dry with materialThe organic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by flash column chromatography (silica)
  11. washeluting with cyclohexane containing
  12. temperatureincreasing amounts of EtOAc affording the title compound as an orange sticky solid

Sources & evidence

ORD record
ord-7ef4a3f7a0d24d67ab5f23748d75e271
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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