Water → 5-(2,5-Difluoro-phenoxy)-furan-2-carbaldehyde

HRID 2080095Notes

Reaction equation

HRID 2080095 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].[H-].[Na+].Br[C:13]1[O:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=1.O>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][C:13]1[O:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 949522,5-DifluorophenolHCID 6003285-Bromofuran-2-carbaldehyde

Product 1

HCID 231306005-(2,5-Difluoro-phenoxy)-furan-2-carbaldehydeYield 22.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,5-difluorophenol (3360 mg, 25.83 mmol) in N,N-dimethylformamide (60 mL) was sodium hydride (1032 mg, 25.83 mmol, 60% in oil), which was then stirred for 1 hour. 5-Bromo-2-furaldehyde (3826 mg, 21.52 mmol) was added to the reaction solution, and the solution was stirred at 60° C. for 12 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and then, concentrated in vacuo. The resulting residue was purified by silica gel chromatography (hexane-ethyl acetate), and the title compound (1104 mg, 4.92 mmol, 22.9%) was obtained.

Workup

  1. stirringthe solution was stirred at 60° C. for 12 hours
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f4ef9bc5624d464f8ad3f3812d0dbd9e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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