Water → 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine

HRID 748624Notes

Reaction equation

HRID 748624 reaction equation
[OH-].[K+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][OH:10].[Cl:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1F.O>C(#N)C>[Cl:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1[O:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11474PiconolHCID 14797Potassium HydroxideHCID 676882-Chloro-1-fluoro-4-nitrobenzene

Product 1

HCID 174694332-((2-Chloro-4-nitrophenoxy)methyl)pyridineYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 160 g of potassium hydroxide and 2-pyridylcarbinol in 8 L acetonitrile was stirred for 20-30 minutes. To this was added 400 g of 3-chloro-4-fluoronitrobenzene and the mixture was stirred at 40° C. for a minimum of 18 hours until the reaction was complete. Water was added and the precipitated yellow solids were filtered and washed with water. The product was dried (40-50° C., 10 mm Hg, 24 h) to the product in 85-95% yield.

Workup

  1. stirringthe mixture was stirred at 40° C. for a minimum of 18 hours until the reaction
  2. filtrationthe precipitated yellow solids were filtered
  3. washwashed with water
  4. customThe product was dried (40-50° C., 10 mm Hg, 24 h) to the product in 85-95% yield

Sources & evidence

ORD record
ord-98509707d1b84e4bbfdc20916a358193
Source dataset
uspto-grants-2008_07
Patent number
US07399865B2

Reaction notes

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