Potassium Carbonate → 2-[1-(3,4-Dichlorophenyl)-2,2,2-trifluoroethoxy]-5-nitropyridine

HRID 1608252Notes

Reaction equation

HRID 1608252 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]([OH:24])[C:20]([F:23])([F:22])[F:21])[CH:15]=[CH:16][C:17]=1[Cl:18].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CS(C)=O>[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]([O:24][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[C:20]([F:21])([F:22])[F:23])[CH:15]=[CH:16][C:17]=1[Cl:18]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 783082-Chloro-5-nitropyridineHCID 136705501-(3,4-Dichlorophenyl)-2,2,2-trifluoroethan-1-ol

Product 1

HCID 136705512-[1-(3,4-Dichlorophenyl)-2,2,2-trifluoroethoxy]-5-nitropyridineYield 89.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Under a dry argon atmosphere a solution of 2-chloro-5-nitropyridine (1.6 g, 0.010 mole) and 1-(3,4-dichlorophenyl)-2,2,2-trifluoroethanol (2.5 g, 0.010 mole) in dimethyl sulfoxide (50 ml) was stirred for five minutes. Potassium carbonate (1.6 g, 0.011 mole) was added to the mixture in one portion. The resultant mixture was stirred at room temperature for approximately 18 hours. The mixture was transferred to a separatory funnel to which was added 50 g of ice and 75 ml of a 2N aqueous sodium hydroxide solution. This aqueous mixture was extracted with two 200 ml portions of diethyl ether. The combined extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated from the filtrate under reduced pressure, leaving an oil. Purification of this oil by column chromatography on silica gel yielded 3.3 g of 2-[1-(3,4-dichlorophenyl)-2,2,2-trifluoroethoxy]-5-nitropyridine.

Workup

  1. customThe mixture was transferred to a separatory funnel to which
  2. extractionThis aqueous mixture was extracted with two 200 ml portions of diethyl ether
  3. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated from the filtrate under reduced pressure
  6. customleaving an oil
  7. customPurification of this oil by column chromatography on silica gel

Sources & evidence

ORD record
ord-6b04885669924d26af895c42e26353ca
Source dataset
uspto-grants-1989_09
Patent number
US04870089

Reaction notes

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