Potassium Carbonate → 4-(2-Fluoro-4-nitrophenoxy)-1-benzofuran

HRID 16409

Reaction equation

HRID 16409 reaction equation
[O:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([OH:10])=[C:4]2[CH:3]=[CH:2]1.[F:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1F.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[F:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1[O:10][C:9]1[C:4]2[CH:3]=[CH:2][O:1][C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 116079214-Benzofuranol

Product 1

HCID 179793424-(2-Fluoro-4-nitrophenoxy)-1-benzofuran

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2.40 g (5.37 mmol) of 1-benzofuran-4-ol (from example XXI), 0.90 g (5.64 mmol) of 3,4-difluoronitrobenzene and 1.48 g (10.7 mmol) of potassium carbonate are suspended in 20 ml of anhydrous dimethylformamide, and the mixture is stirred at 50° C. for 5 hours. The reaction solution is then diluted with water and extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate. The solvent is removed under reduced pressure. The crude product is purified on a silica gel column (mobile phase: cyclohexane:ethyl acetate (10:1)).

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. customThe solvent is removed under reduced pressure
  4. customThe crude product is purified on a silica gel column (mobile phase: cyclohexane:ethyl acetate (10:1))

Sources & evidence

ORD record
ord-8853a30f4ce14b6984728337f449eb95
Source dataset
uspto-grants-2010_06
Patent number
US07737153B2

Linked notes

Loading…