Potassium Carbonate → 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine

HRID 877084Notes

Reaction equation

HRID 877084 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.C([O-])([O-])=O.[K+].[K+].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][OH:25]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:25][CH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11474PiconolHCID 676882-Chloro-1-fluoro-4-nitrobenzene

Product 1

HCID 174694332-((2-Chloro-4-nitrophenoxy)methyl)pyridineYield 77.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 2-chloro-1-fluoro-4-nitro-benzene (8.75 g, 50 mmol) in dry Acetone (100 ml) was added 10.0 g of K2CO3 and 5.45 g of 2-pyridylmethanol (50 mmol). The reaction mixture was then stirred at 65° C. overnight. Filtration and concentration gave a solid which was recrystallized to give the desired product as a white solid (10.2 g).

Workup

  1. filtrationFiltration and concentration
  2. customgave a solid which
  3. customwas recrystallized

Sources & evidence

ORD record
ord-1df7411a1d174a5c96784348fd166d50
Source dataset
uspto-grants-2015_03
Patent number
US08987284B2

Reaction notes

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