Carbon tetrabromide → 4-(3-Bromopropyl)benzonitrile

HRID 899115Notes

Reaction equation

HRID 899115 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:33]>C(Cl)Cl>[Br:33][CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 110841784-(3-Hydroxypropyl)benzonitrile

Product 1

HCID 4583644-(3-Bromopropyl)benzonitrileYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(3-hydroxypropyl)benzonitrile (13 g, 0.081 mol; see step (iii) above) and triphenylphosphine (42.3 g, 0.16 mol) in DCM (150 mL) was added, dropwise at 0-5° C., a solution of CBr4 (53.5 g, 0.16 mol) in DCM (100 mL). The resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the product was purified by column chromatography over silica gel, using petroleum ether in ethyl acetate as eluent, to yield 12.5 g (69%) of the sub-title compound as a yellow liquid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe product was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-6f2c0564238b47639802acd53a890f0a
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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