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

HRID 1449212Notes

Reaction equation

HRID 1449212 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-105078307eee4d06b84fd5d3dbf9c4e1
Source dataset
uspto-grants-1980_02
Patent number
US04189500

Reaction notes

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