4-Bromo-2-fluoroanisole → 3-Fluoro-4-methoxybenzonitrile

HRID 1992363Notes

Reaction equation

HRID 1992363 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([F:10])[CH:3]=1.[C:11]([Cu])#[N:12]>CN(C=O)C.O>[F:10][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[O:8][CH3:9])[C:11]#[N:12]

Participants

5

Reactant 2

HCID 753784-Bromo-2-fluoroanisoleHCID 178418546HCID 178418546, compound

Product 1

HCID 27745483-Fluoro-4-methoxybenzonitrileYield 30.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-Bromo-2-fluoro-1-methoxybenzene (107 g, 0.5244 mol, from step (ii) above), CuCN (70.4 g, 0.7866 mol) in dry DMF (150 ml) was stirred at 120° C. overnight. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. Organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporation under reduced pressure followed by column chromatography over silica gel using 3% ethyl acetate in petroleum ether gave the sub-title compound (24.4 g) as a solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washOrganic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-028e76ec5432403caf495f89061b9038
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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