Phosphorus tribromide → (6-Bromohex-3-en-1-yl)benzene

HRID 1680747Notes

Reaction equation

HRID 1680747 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]([CH:11]2[CH2:13][CH2:12]2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:15].[Br-].[Li+]>[Br-].[Zn+2].[Br-]>[C:1]1([CH2:7][CH2:8][CH:9]=[CH:11][CH2:12][CH2:13][Br:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 82050Lithium BromideHCID 10899201HCID 10899201, compound

Product 1

HCID 53420932(6-Bromohex-3-en-1-yl)benzene

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Procedure

6-Phenyl-3-hexenyl bromide [V; Ar is C6H5, R is H] was prepared from 16.5 g. of 2-phenylethyl cyclopropyl carbinol (Preparation B6), 21.5 g. of phosphorus tribromide, 17.65 g. of lithium bromide and 20.7 g. of zinc bromide according to the procedure given above in Preparation C1, affording 21 g. of product as a pale yellow oil.

Workup

  1. customaffording 21 g

Sources & evidence

ORD record
ord-27b944afb35d41b58f46f75304df81ca
Source dataset
uspto-grants-1981_06
Patent number
US04275201

Reaction notes

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