Phosphine tribromide → 4'-(Bromomethyl)-2'-nitrobiphenyl-2-carbonitrile

HRID 519878Notes

Reaction equation

HRID 519878 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([N+:17]([O-:19])=[O:18])[CH:4]=1.[Br-:20].[Br-].[Br-].P>C1(C)C=CC=CC=1>[Br:20][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([N+:17]([O-:19])=[O:18])[CH:4]=1

Participants

4

Reactant 2

HCID 21862892Phosphine tribromideHCID 670092004'-(Hydroxymethyl)-2'-nitrobiphenyl-2-carbonitrile

Product 1

HCID 670096674'-(Bromomethyl)-2'-nitrobiphenyl-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution (15 mL) of 4′-(hydroxymethyl)-2′-nitrobiphenyl-2-carbonitrile (3.62 g) in toluene was added phosphine tribromide (4.63 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 4′-(bromomethyl)-2′-nitrobiphenyl-2-carbonitrile as a pale-yellow oil.

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-591fda5b610847af9fb71f144ff15531
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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