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

HRID 1704162Notes

Reaction equation

HRID 1704162 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 the Preparation C1, affording 19 g. of product as an oil.

Workup

  1. customaffording 19 g

Sources & evidence

ORD record
ord-a4c653a86bf84b6ea5499c31a60464e3
Source dataset
uspto-grants-1978_11
Patent number
US04125714

Reaction notes

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