Phosphorus tribromide → 3-Methyl-6-(3,4-methylenedioxyphenyl)-3-hexenyl bromide

HRID 1680744Notes

Reaction equation

HRID 1680744 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][CH:12]([C:14]3([CH3:17])[CH2:16][CH2:15]3)O)=[CH:4][C:3]=2[O:2]1.P(Br)(Br)[Br:19].[Br-].[Li+]>[Br-].[Zn+2].[Br-]>[CH3:17][C:14](=[CH:12][CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)[CH2:15][CH2:16][Br:19]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 82050Lithium BromideHCID 234557382-(3,4-Methylenedioxyphenyl)ethyl 1-methycyclopropyl carbinol

Product 1

HCID 545086813-Methyl-6-(3,4-methylenedioxyphenyl)-3-hexenyl bromide

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Procedure

3-Methyl-6-(3,4-methylenedioxyphenyl)-3-hexenyl bromide [V; Ar is 3,4-methylenedioxyphenyl, R is CH3 ] was prepared from 17.6 g. of 2-(3,4-methylenedioxyphenyl)ethyl 1-methylcyclopropyl carbinol (Preparation B3), 20.3 g. of phosphorus tribromide, 18.5 g. of lithium bromide and 21 g. of zinc bromide according to the procedure given above in Preparation C1, affording 19 g. of product as an oil.

Workup

  1. customaffording 19 g

Sources & evidence

ORD record
ord-1872af1d3a424e6fad80bc64bd9e2014
Source dataset
uspto-grants-1981_06
Patent number
US04275201

Reaction notes

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