Carbon tetrabromide → 4-(1-Bromoethyl)benzonitrile

HRID 1292686Notes

Reaction equation

HRID 1292686 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-8400164f6e6e4528b670fc56db847540
Source dataset
uspto-grants-1998_05
Patent number
US05756528

Reaction notes

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