Dimethyl Sulfoxide → 5-Nitro-2-(2,2,2-trifluoroethoxy)pyridine

HRID 46465Notes

Reaction equation

HRID 46465 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[F:11][C:12]([F:16])([F:15])[CH2:13][OH:14].[OH-].[Li+].CS(C)=O>O>[F:11][C:12]([F:16])([F:15])[CH2:13][O:14][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 3939Lithium HydroxideHCID 64092,2,2-TrifluoroethanolHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 6137185-Nitro-2-(2,2,2-trifluoroethoxy)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloro-5-nitropyridine (9.5 grams), 2,2,2-trifluoroethanol (6.0 grams), and lithium hydroxide (4.0 grams) were mixed in 50 ml. of DMSO and stirred overnight (about 18 hours) at room temperature. The reaction mixture was then poured into water and the product was separated by filtration. It was crystallized from ethyl acetate-hexanes, yield 5.0 grams, m.p., 35°-37° C.

Workup

  1. customthe product was separated by filtration
  2. customIt was crystallized from ethyl acetate-hexanes, yield 5.0 grams
  3. custom35°-37° C.

Sources & evidence

ORD record
ord-558bb867ab5c4bd4a3b4e2b03e7cc939
Source dataset
uspto-grants-1979_11
Patent number
US04173639

Reaction notes

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