1,3-Dibromopropane → 4-(3-Bromopropoxy)-3,5-difluorobenzonitrile

HRID 1992378Notes

Reaction equation

HRID 1992378 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([F:10])[C:3]=1[OH:11].[Br:12][CH2:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:12][CH2:13][CH2:14][CH2:15][O:11][C:3]1[C:2]([F:1])=[CH:7][C:6]([C:8]#[N:9])=[CH:5][C:4]=1[F:10]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 107494063,5-Difluoro-4-hydroxy-benzonitrile

Product 1

HCID 685200304-(3-Bromopropoxy)-3,5-difluorobenzonitrileYield 91.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,6-difluoro-4-cyanophenol (6 g, 0.038 mol), 1,3-dibromopropane (46.9 g, 0.23 mol) and dry potassium carbonate (8 g, 0.058 mol) in dry DMF (50 ml) was stirred at RT overnight under nitrogen atmosphere. Solvent was removed under reduced pressure and the residue was purified by column chromatography over silica gel using 4% ethyl acetate in petroleum ether as eluent to yield (9.6 g) of the title compound as a liquid.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography over silica gel using 4% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-5e9bc65c4a464ee4a0296fb09f408e6f
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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