4-Fluorophenol → 5-(4-Fluorophenoxy)furan-2-carbaldehyde

HRID 2080147Notes

Reaction equation

HRID 2080147 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[N+]([C:14]1[O:18][C:17]([CH:19]=[O:20])=[CH:16][CH:15]=1)([O-])=O>CS(C)=O.[Cl-].[Na+].O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:14]2[O:18][C:17]([CH:19]=[O:20])=[CH:16][CH:15]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 127745-NitrofurfuralHCID 24758Sodium hydride

Product 1

HCID 110419065-(4-Fluorophenoxy)furan-2-carbaldehydeYield 98%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 4-fluorophenol (2.39 g, 21.3 mmol) in dimethylsulfoxide (20 mL) was added sodium hydride (785 mg, 19.6-23.6 mmol, 60-72% in oil), and the solution was stirred at room temperature for 20 minutes. Next, a solution of 5-nitro-furan-2-carbaldehyde (3 g, 21.3 mmol) in dimethylsulfoxide (10 mL) was added dropwise, the solution was then stirred for 2 hours at room temperature. The reaction mixture was poured into brine, and the mixture was extracted with ethyl acetate. The fractionated organic layer was dried over anhydrous magnesium sulfate, then concentrated, and the title compound (4.3 g, 20.8 mmol, 98%) was obtained.

Workup

  1. stirringthe solution was then stirred for 2 hours at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe fractionated organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9c8ca423efeb4d7e9a60dbcdb1fa6a88
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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