4-Bromo-2,6-difluoroanisole → 3,5-Difluoro-4-methoxybenzonitrile

HRID 2078403Notes

Reaction equation

HRID 2078403 reaction equation
[CH3:1][O:2][C:3]1[C:8]([F:9])=[CH:7][C:6](Br)=[CH:5][C:4]=1[F:11].[C:12]([Cu])#[N:13]>CN(C=O)C.O>[F:11][C:4]1[CH:5]=[C:6]([CH:7]=[C:8]([F:9])[C:3]=1[O:2][CH3:1])[C:12]#[N:13]

Participants

5

Reactant 2

HCID 27732874-Bromo-2,6-difluoroanisoleHCID 178418546HCID 178418546, compound

Product 1

HCID 105832533,5-Difluoro-4-methoxybenzonitrileYield 30.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromo-2,6-difluorophenyl methyl ether (11.5 g, 0.0516 mol; see step (ii) above) and CuCN (6.92 g, 0.0774 mol) in dry DMF (15 mL) was stirred at 120° C. for two days under nitrogen atmosphere. 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 dried over sodium sulfate. Solvent evaporation under reduced pressure followed by column chromatography over silica gel, using 2% ethyl acetate in petroleum ether as eluent, yielded 2.7 g of the sub-title compound as a pale yellow 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-1850d6c37fd440f4b5856c6ca57a6405
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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