Phosphorus tribromide → 4-(3-Bromopropoxy)-3-fluorobenzonitrile

HRID 1992380Notes

Reaction equation

HRID 1992380 reaction equation
P(Br)(Br)[Br:2].[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH2:16][CH2:17]O)[C:9]#[N:10]>C(Cl)(Cl)(Cl)Cl>[Br:2][CH2:17][CH2:16][CH2:15][O:14][C:13]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[F:5]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 436575093-Fluoro-4-(3-hydroxypropoxy)-benzonitrile

Product 1

HCID 685196304-(3-Bromopropoxy)-3-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

PBr3 (8.14 g, 0.03 mol) was added drop by drop at 0° C. to a solution of 3-fluoro-4-(3-hydroxypropoxy)-benzonitrile (5.5 g, 0.028 mol, from step (i) above in carbon tetrachloride (50 ml) and stirred at room temperature overnight under nitrogen atmosphere. The reaction was quenched with water, and extracted with dichloromethane. Organic layer was washed with water, brine, dried over sodium sulfate and solvent evaporated under reduced pressure. The residue was purified by column chromatography over silica gel using 6% ethyl acetate in petroleum ether as eluent to yield (4.3 g) of the title compound as a liquid.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. washOrganic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate and solvent
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel using 6% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-1d2dae3589bc46c1908b7b75f3d0e759
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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