Cesium carbonate → HCID 89611382, compound

HRID 2174936Notes

Reaction equation

HRID 2174936 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[OH:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[F:9][C:8]([F:11])([F:10])[C:5]1[N:6]=[CH:7][C:2]([O:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 130194-CyanophenolHCID 27611975-Bromo-2-(trifluoromethyl)pyridine

Product 1

HCID 89611382HCID 89611382, compound

Reagents, catalysts & solvents 3

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2.5 g of 5-bromo-2-(trifluoromethyl)pyridine, 5.8 g of 4-hydroxybenzonitrile, 10.8 g of caesium carbonate and 1.87 g of molybdenum hexacarbonyl in 100 ml 1,4-dioxan were heated under reflux until complete conversion. The reaction mixture was diluted with water, extracted several times with ethyl acetate, and the combined organic phases washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated. The residue was purified by column chromatography on silica gel using a hexane/ethyl acetate gradient. Yield: 1.35 g of the title compound.

Workup

  1. temperatureunder reflux until complete conversion
  2. extractionextracted several times with ethyl acetate
  3. washthe combined organic phases washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel using a hexane/ethyl acetate gradient

Sources & evidence

ORD record
ord-609f745ec491493b97ab8d4376e727f3
Source dataset
uspto-grants-2015_06
Patent number
US09062041B2

Reaction notes

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