Carbon tetrabromide → 4-(1-Bromoethyl)benzonitrile

HRID 1741491Notes

Reaction equation

HRID 1741491 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9](O)[CH3:10])=[CH:5][CH:4]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>C(OCC)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([Br:32])[CH3:10])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5833354-(1-Hydroxyethyl)benzonitrile

Product 1

HCID 218346374-(1-Bromoethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-(4-Cyanophenyl)ethanol 1.01 g, 6.84 mmol), in diethyl ether (15 ml) and triphenylphosphine (2.14 g, 8.17 mmol), was added carbon tetrabromide (2.82 g, 8.50 mmol) in dieathylether (20 ml) at room temperature. After 30 min the reaction was filtered through celite and evaporated to dryness. The residue was purified by chromatography (SiO2, 5% EtOAc in hexanes) to afford the title compound as an oil

Workup

  1. filtrationAfter 30 min the reaction was filtered through celite
  2. customevaporated to dryness
  3. customThe residue was purified by chromatography (SiO2, 5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0c1d7562d1dd4bf69493a6ded17bde2b
Source dataset
uspto-grants-1999_10
Patent number
US05972984

Reaction notes

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