4-Fluorophenol → 2-(4-fluorophenoxy)-3-nitropyridine

HRID 1988851Notes

Reaction equation

HRID 1988851 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:12]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19]>CN(C)C=O.C(OCC)(=O)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:14]2[C:13]([N+:18]([O-:20])=[O:19])=[CH:12][CH:17]=[CH:16][N:15]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 27374582-(4-fluorophenoxy)-3-nitropyridineYield 77.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (7.2 g, 180.4 mmol) was slowly added at 0° C. to a solution of 4-fluorophenol (17.11 g, 152.6 mmol) in 200 ml of N,N-dimethylformamide and then the reaction mixture was stirred for 30 minutes at room temperature. 4-Chloro-3-nitropyridine (22.0 g, 138.8 mmol) prepared in Step 1 of Preparation 1 was added at 0° C. to the reaction mixture, which was stirred for 1 hour at room temperature, diluted with 200 ml of ethyl acetate, and then washed with 200 ml of water three times. The separated organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure to give the titled compound as a pale yellow solid (25.2 g, 76.8%).

Workup

  1. additionwas added at 0° C. to the reaction mixture, which
  2. stirringwas stirred for 1 hour at room temperature
  3. washwashed with 200 ml of water three times
  4. dry with materialThe separated organic layer was dried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fbfd88445fc04b6f809f8439c7c831bb
Source dataset
uspto-grants-2010_01
Patent number
US07642269B2

Reaction notes

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