Iodoethane → 3-Bromo-2-ethoxy-5-(trifluoromethyl)pyridine

HRID 1976058Notes

Reaction equation

HRID 1976058 reaction equation
I[CH2:2][CH3:3].[Br:4][C:5]1[C:6](=[O:15])[NH:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1>CCCCCC.C(=O)([O-])[O-].[Ag+2]>[Br:4][C:5]1[C:6]([O:15][CH2:2][CH3:3])=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:12])[F:13])[CH:10]=1

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 134917753-Bromo-5-(trifluoromethyl)pyridin-2(1H)-one

Product 1

HCID 225912723-Bromo-2-ethoxy-5-(trifluoromethyl)pyridineYield 59.8%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 8058HexaneSolvent

Procedure

Iodoethane (1.33 ml, 16.6 mmol) was added to a suspension of 3-bromo-5-trifluoromethyl-2(1H)-pyridone (2.0 g, 8.3 mmol) and silver carbonate (1.16 g, 4.2 mmol) in hexane (50 ml) and the mixture stirred for 64 h at room temperature. The resulting suspension was filtered, the filtrate evaporated and the residue purified by chromatography on silica gel to give the product as a colourless oil (1.34 g).

Workup

  1. filtrationThe resulting suspension was filtered
  2. customthe filtrate evaporated
  3. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-3762bd3f9f1347999f4ecd7f584e10b9
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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