Bromopinacolone → HCID 20330256, compound

HRID 1862833Notes

Reaction equation

HRID 1862833 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.Br[CH2:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13]>CCCCCC.C(=O)([O-])[O-].[Ag+2]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 21642BromopinacoloneHCID 1785160645-chloropyridin-2-ol

Product 1

HCID 20330256HCID 20330256, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 8058HexaneSolvent

Procedure

A mixture of 12.96 grams (g) (0.1 mole) of 5-chloro-2-hydroxypyridine, 17.9 g (0.1 mole) of 1-bromo-3,3-dimethyl-2-butanone, and 15 g (0.054 mole) of silver carbonate in hexane was stirred and heated at reflux temperature for 48 hours. The reaction mixture was filtered, and the solvent removed by evaporation. The residue was dissolved in methylene chloride and filtered through silica gel. Evaporation of the solvent gave 10.5 g (46 percent (%) yield) of 1-(5-chloro-2-pyridinyloxy)-3,3-dimethyl-2-butanone. A sample recrystallized from pentane had a melting point of 68°-69.5° C.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 48 hours
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent removed by evaporation
  5. dissolutionThe residue was dissolved in methylene chloride
  6. filtrationfiltered through silica gel
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-9f9f767d0b774682b46d12f9605725c9
Source dataset
uspto-grants-1979_09
Patent number
US04166854

Reaction notes

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