Water → 2-[(4-Nitrophenoxy)methyl]pyridine

HRID 2236525Notes

Reaction equation

HRID 2236525 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[H-].[Na+].F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.O>CN(C)C=O>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([O:8][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11474PiconolHCID 24758Sodium hydride

Product 1

HCID 8209312-[(4-Nitrophenoxy)methyl]pyridineYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

An amount of 1.36 mL (14.14 mmol) of pyridin-2-yl-methanol is dissolved in N,N-dimethylformamide (10 mL) and cooled to 0° C., addition of 678.72 mg (28.28 mmol) of sodium hydride followed. The reaction mixture is kept at 0° C. for 1.5 hours. 1-Fluoro-4-nitrobenzene 1.5 mL (14.14 mmol) is subsequent added and stirred at room temperature overnight. 100 mL of water is added to the mixture and stirred for 10 more mins. The precipitate is filtered and washed many times with water. The white solid is re-dissolved in methylene chloride extracted three times with brine, dried over darko and magnesium sulfate, and evaporated to give the desired product as a white solid 2.7 g (85% yield); mp: 116-117° C.

Workup

  1. stirringstirred for 10 more mins
  2. filtrationThe precipitate is filtered
  3. washwashed many times with water
  4. dissolutionThe white solid is re-dissolved in methylene chloride
  5. extractionextracted three times with brine
  6. dry with materialdried over darko and magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-0a8dff7860574a5a8438f67eaae22d6e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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