Phosphorus tribromide → 4'-(Bromomethyl)-2'-fluorobiphenyl-2-carbonitrile

HRID 1412260Notes

Reaction equation

HRID 1412260 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][C:3]=1[C:10]1[C:11]([C:16]#[N:17])=[CH:12][CH:13]=[CH:14][CH:15]=1.P(Br)(Br)[Br:19].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Br:19][CH2:8][C:6]1[CH:5]=[CH:4][C:3]([C:10]2[C:11]([C:16]#[N:17])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 670099902'-Fluoro-4'-(hydroxymethyl)biphenyl-2-carbonitrile

Product 1

HCID 670084324'-(Bromomethyl)-2'-fluorobiphenyl-2-carbonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution (150 mL) of 2′-fluoro-4′-(hydroxymethyl)biphenyl-2-carbonitrile (14.1 g) in toluene was added phosphorus tribromide (18.7 g) at room temperature, and the mixture was stirred for 16 hr. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture, and the solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate, and the obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (15.3 g, 100%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washthe obtained ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d94e336287aa494c9d6bfb9ac8dae557
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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