4-(3-Bromopropoxy)-3-fluorobenzonitrile → 4-Methoxybenzene-1,3-dicarbonitrile

HRID 2078416Notes

Reaction equation

HRID 2078416 reaction equation
BrCC[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1F.[C:15]([Cu])#[N:16]>CN(C=O)C.O>[CH3:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[C:15]#[N:16]

Participants

5

Reactant 2

HCID 685196304-(3-Bromopropoxy)-3-fluorobenzonitrileHCID 178418546HCID 178418546, compound

Product 1

HCID 50619954-Methoxybenzene-1,3-dicarbonitrileYield 47.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

2,4-Dibromo-1-methoxybenzene (25 g, 0.094 mol; see step (i) above) was dissolved in dry DMF (50 mL). CuCN (25.3 g, 0.283 mol) was then added and the resulting mixture was stirred at 120° C. for 15 h, before being cooled to RT. The crude mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel, using 25% ethyl acetate in petroleum ether as eluent, to yield the sub-title compound (7.1 g, 24%) as pale yellow solid.

Workup

  1. temperaturebefore being cooled to RT
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-1cdf8932ab254c6b9eca0bb7b9a817c2
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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