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

HRID 2078405Notes

Reaction equation

HRID 2078405 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[OH:10])[C:5]#[N:6].C([O-])([O-])=O.[K+].[K+].[Br:18][CH2:19][CH2:20][CH2:21]Br>CN(C=O)C>[Br:18][CH2:19][CH2:20][CH2:21][O:10][C:9]1[C:2]([F:1])=[CH:3][C:4]([C:5]#[N:6])=[CH:7][C:8]=1[F:11]

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 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3,5-difluoro-4-hydroxybenzonitrile (2.1 g, 0.0136 mol; see step (iv) above), K2CO3 (3.76 g, 0.0272 mol) and 1,3-dibromopropane (16.48 g, 0.0816 mol) in dry DMF (50 mL) was stirred at 60° C. overnight under a nitrogen atmosphere. The reaction mixture was filtered through Celite® and partitioned between water and ethyl acetate. The organic layer was washed with water and brine and then dried over sodium sulfate. Solvent evaporation under reduced pressure provided a residue that was purified by column chromatography over silica gel, using 2.5% ethyl acetate in petroleum ether as eluent, to yield 1.5 g (20%) of the sub-title compound as a yellow liquid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. custompartitioned between water and 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
  6. customprovided a residue that
  7. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-1c00addd66f94f968ab6baa1e0c22b3b
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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