Potassium Carbonate → 5-(2-Chloro-4-nitrophenoxy)-2-methylpyridine

HRID 2105302Notes

Reaction equation

HRID 2105302 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1F>CC(C)=O.CCOC(C)=O>[Cl:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[O:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[N:7][CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 142752-Methyl-5-hydroxypyridineHCID 676882-Chloro-1-fluoro-4-nitrobenzene

Product 1

HCID 470785965-(2-Chloro-4-nitrophenoxy)-2-methylpyridine

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

6-methyl-pyridin-3-ol Compound 80b (3.10 g, 28.4 mmol) and potassium carbonate (7.80 g, 56.8 mmol) were added to a solution of 2-chloro-1-fluoro-4-nitro-benzene Compound 80a (5.0 g, 28.4 mmol) in acetone (50 mL). The suspension was refluxed for 20 hrs and then cooled to 25° C. The reaction mixture was diluted with EtOAc and washed with water and brine. The organic solution was dried over Na2SO4, then filtered and concentrated to yield 5-(2-chloro-4-nitro-phenoxy)-2-methyl-pyridine Compound 80c (5.6 g, 80%). MS 350 (M−).

Workup

  1. temperatureThe suspension was refluxed for 20 hrs
  2. washwashed with water and brine
  3. dry with materialThe organic solution was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7b596c29064d47ce9101ab12996d0b2a
Source dataset
uspto-grants-2009_08
Patent number
US07579356B2

Reaction notes

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