Cesium fluoride → HCID 24825845, compound

HRID 2043313Notes

Reaction equation

HRID 2043313 reaction equation
Br[C:2]1=[CH:3][C:4](=[O:9])[O:5]/[C:6]/1=[CH:7]\Br.[S:10]1[CH:14]=[CH:13][C:12](B(O)O)=[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>[S:10]1[CH:14]=[CH:13][C:12]([C:2]2=[CH:3][C:4](=[O:9])[O:5]/[C:6]/2=[CH:7]\[C:12]2[CH:13]=[CH:14][S:10][CH:11]=2)=[CH:11]1

Participants

9

Reactant 3

HCID 25953Cesium fluorideHCID 581760Thiophene-3-boronic acidHCID 10131246HCID 10131246, compound

Product 1

HCID 24825845HCID 24825845, compound

Reagents, catalysts & solvents 5

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

Procedure

A mixture containing (Z)-4-bromo-5-(bromomethylene)furan-2(5H)-one (0.502 g, 1.977 mmol), 3-thiopheneboronic acid (0.553 g, 4.322 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.068 g, 9.688×10−2 mmol), tetrabutylammonium iodide (0.037 g, 1.137×10−1 mmol) and cesium fluoride (1.221 g, 8.038 mmol) in toluene (10 mL) and water (10 mL) was stirred at room temperature for 72 h under nitrogen. Brine (50 mL) was added and the product extracted with ethyl acetate (3×50 mL). The organic fractions were combined, washed with brine (3×20 mL), dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure to give a dark brown solid. The resulting solid was subjected to recrystallization to give (Z)-4-(thiophen-3-yl)-5-(thiophen-3-ylmethylene)furan-2(5H)-one 18.

Workup

  1. extractionthe product extracted with ethyl acetate (3×50 mL)
  2. washwashed with brine (3×20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customto give a dark brown solid
  6. customThe resulting solid was subjected to recrystallization

Sources & evidence

ORD record
ord-7e462f5bfa7f4ab89bbdb37fa2a3701f
Source dataset
uspto-grants-2013_11
Patent number
US08586618B2

Reaction notes

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