Water → HCID 86674219, compound

HRID 1425594Notes

Reaction equation

HRID 1425594 reaction equation
[H-].[Na+].[N+:3]([C:6]1[C:7]([C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)=[N:8][CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4].Br[CH2:20][CH2:21][F:22].O>CN(C=O)C>[F:22][CH2:21][CH2:20][O:18][C:14]1[CH:13]=[C:12]([C:7]2[C:6]([N+:3]([O-:5])=[O:4])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 129822-Fluoroethyl bromideHCID 24758Sodium hydrideHCID 71059442HCID 71059442, compound

Product 1

HCID 86674219HCID 86674219, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride 60% (0.021 g, 0.925 mmol) was added to a solution containing 3-(3-nitropyridin-2-yl)phenol (0.2 g, 0.925 mmol) and 1-Bromo-2-fluoroethane (0.138 ml, 1.850 mmol) in DMF (Volume: 3.08 ml). The reaction was stirred for 2 hours. Diluted reaction with water and extracted with ethyl acetate. Combined organics, dried, filtered, and purified by ISCO column using 35% ethyl acetate in hexanes to afford 2-(3-(2-fluoroethoxy)phenyl)-3-nitropyridine (0.11 g, 0.419 mmol, 45.3% yield).

Workup

  1. additionDiluted
  2. extractionextracted with ethyl acetate
  3. customCombined organics, dried
  4. filtrationfiltered
  5. custompurified by ISCO column

Sources & evidence

ORD record
ord-c40fcc859e4e488b99151f8be63d88a8
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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