Phenol → HCID 117921020, compound

HRID 594200Notes

Reaction equation

HRID 594200 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1.[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[N+:8]([C:7]1[C:2]([O:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:3][CH:4]=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 47369502-Chloro-3-nitro-5-(trifluoromethyl)pyridine

Product 1

HCID 117921020HCID 117921020, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-chloro-3-nitro-5-(trifluoromethyl)pyridine (1280 mg) in dimethylformamide (18 mL) were added phenol (800 mg) and cesium carbonate (5530 mg). The reaction mixture was stirred at 60° C. for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with water and a saturated sodium chloride aqueous solution. The obtained organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified on silica gel column chromatography (hexane:ethyl acetate=1:19) to give the titled compound (370 mg) having the following physical data.

Workup

  1. washwashed with water
  2. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified on silica gel column chromatography (hexane:ethyl acetate=1:19)

Sources & evidence

ORD record
ord-c174efe81cc54496b116bfa2656cb8bd
Source dataset
uspto-grants-2016_01
Patent number
US09242977B2

Reaction notes

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