Phosphine tribromide → 2-[5-(Bromomethyl)thiophen-2-yl]benzonitrile

HRID 1412578Notes

Reaction equation

HRID 1412578 reaction equation
O[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])=[CH:5][CH:4]=1.[Br-:16].[Br-].[Br-].P>C1(C)C=CC=CC=1>[Br:16][CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 21862892Phosphine tribromideHCID 670088992-[5-(Hydroxymethyl)thiophen-2-yl]benzonitrile

Product 1

HCID 670086562-[5-(Bromomethyl)thiophen-2-yl]benzonitrileYield 121.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution (50 mL) of 2-[5-(hydroxymethyl)thiophen-2-yl]benzonitrile (2.60 g) in toluene was added phosphine tribromide (2.60 g) at room temperature, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate. The obtained ethyl acetate solution was washed with saturated aqueous sodium hydrogen carbonate and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (3.20 g, 95%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe obtained ethyl acetate solution was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-27cfd1557dde46019c764d680c5404da
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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