Potassium Phosphate, Tribasic → HCID 17842600, compound

HRID 1403385Notes

Reaction equation

HRID 1403385 reaction equation
Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[OH:11].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.O.[Cu]I>[F:10][C:7]1[CH:8]=[CH:9][C:4]2[CH:3]=[CH:2][O:11][C:5]=2[CH:6]=1

Participants

6

Reactant 2

HCID 62657Potassium Phosphate, TribasicHCID 86670559HCID 86670559, compound

Product 1

HCID 17842600HCID 17842600, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(2,2-dibromoethenyl)-5-fluorophenol (580 mg, 1.96 mmol) in tetrahydrofuran (20 mL) was added CuI (30 mg, 0.16 mmol), K3PO4 (800 mg, 3.77 mmol) under nitrogen atmosphere. After stirring overnight at 80° C., the reaction mixture was dissolved in water (50 mL), extracted with dichloromethane (3×30 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford a residue, which was purified by a silica gel column with petroleum ether to afford 6-fluoro-1-benzofuran as a white solid (0.16 g, 38%).

Workup

  1. extractionextracted with dichloromethane (3×30 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford a residue, which
  5. customwas purified by a silica gel column with petroleum ether

Sources & evidence

ORD record
ord-fc09be538fb34218afbeac31c1d3d502
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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