Cesium fluoride → HCID 68547678, compound

HRID 2043310Notes

Reaction equation

HRID 2043310 reaction equation
Br[C:2]1[C:6](=[CH:7][Br:8])[O:5][C:4](=[O:9])[CH:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[F-].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O.[Cl-].[Na+].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>[C:10]1([C:2]2[C:6](=[CH:7][Br:8])[O:5][C:4](=[O:9])[CH:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

9

Reactant 3

HCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 67228456HCID 67228456, compound

Product 1

HCID 68547678HCID 68547678, compound

Reagents, catalysts & solvents 5

HCID 67553Tetrabutylammonium IodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture containing 4-bromo-5-bromomethylene-2(5H)-furanone (1 mmol), phenylboronic acid (2.2 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.05 mmol), tetrabutylammonium iodide (0.05 mmol) and cesium fluoride (3 mmol) in toluene (10 mL) and water (10 mL) were stirred for 48-72 h under nitrogen at room temperature. Brine (50 mL) was added and the product extracted with ethyl acetate (3×50 mL). The organic fractions were combined, washed with brine (3×50 mL), dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure. The resulting solid was chromatographed (silica gel: eluent 25:75 dichloromethane/light petroleum, 50:50 dichloromethane/light petroleum or 100% dichloromethane) giving the desired product—4-phenyl-5-bromomethylene-2-(5H)-furanone.

Workup

  1. extractionthe product extracted with ethyl acetate (3×50 mL)
  2. washwashed with brine (3×50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customThe resulting solid was chromatographed (silica gel: eluent 25:75 dichloromethane/light petroleum, 50:50 dichloromethane/light petroleum or 100% dichloromethane)

Sources & evidence

ORD record
ord-c8a20701a1924720b091d0780f92950c
Source dataset
uspto-grants-2013_11
Patent number
US08586618B2

Reaction notes

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