Ethyl Acetate → HCID 57479256, compound

HRID 2105264Notes

Reaction equation

HRID 2105264 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[H-].[Na+].Br[C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][N:17]=1.C(OCC)(=O)C>CN(C=O)C>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([O:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:9][CH:8]=2)=[N:17][CH:18]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 693532,5-DibromopyridineHCID 70015p-(Trifluoromethoxy)phenol

Product 1

HCID 57479256HCID 57479256, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a mixture of 4-trifluoromethoxyphenol (4.4 ml) and sodium hydride (60% dispersion in mineral oil, 1.35 g) in dry DMF (3 ml) was added a solution of 2,5-dibromopyridine in dry DMF (3 mL). The mixture was heated at 60° C. for 8 h. Upon cooling, ethyl acetate was added and the mixture was washed with NH4Cl 1N. The organic layer was dried (Na2SO4) and the solvent evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluent:AcOEt/Hexane 1:10) to afford 1.08 g of the title compound as a colorless oil.

Workup

  1. temperatureUpon cooling
  2. washthe mixture was washed with NH4Cl 1N
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent evaporated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel (eluent:AcOEt/Hexane 1:10)

Sources & evidence

ORD record
ord-26741678d8074935a78731479940e208
Source dataset
uspto-grants-2009_08
Patent number
US07579353B2

Reaction notes

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