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

HRID 2078410Notes

Reaction equation

HRID 2078410 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 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromo-2-fluoro-1-methoxybenzene (107 g, 0.52 mol; see step (ii) above), CuCN (70.4 g, 0.78 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. The organic layer was washed with water and brine and then dried over sodium sulfate. Solvent evaporation under reduced pressure, followed by column chromatography over silica gel using 3% ethyl acetate in petroleum ether as eluent, gave 24.4 g of the sub-title compound as a solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic 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-47c5fbe209104485bb586f4e214dbf56
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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