Cesium fluoride → HCID 24825846, compound

HRID 2043314Notes

Reaction equation

HRID 2043314 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][CH:12]=[C:11]1B(O)O.[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][CH:12]=[C:11]1[C:2]1=[CH:3][C:4](=[O:9])[O:5]/[C:6]/1=[CH:7]\[C:11]1[S:10][CH:14]=[CH:13][CH:12]=1

Participants

9

Reactant 3

HCID 25953Cesium fluorideHCID 27339602-Thiopheneboronic acidHCID 10131246HCID 10131246, compound

Product 1

HCID 24825846HCID 24825846, 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 (0.503 g, 1.981 mmol), 2-thiopheneboronic acid (0.560 g, 4.377 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.072 g, 1.026×10−1 mmol), tetrabutylammonium iodide (0.072 g, 1.002×10−1 mmol) and cesium fluoride (1.257 g, 8.275 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-2-yl)-5-(thiophen-2-ylmethylene)furan-2(5H)-one 19.

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-0c4b88b6c0f94bca804475437b5e31df
Source dataset
uspto-grants-2013_11
Patent number
US08586618B2

Reaction notes

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