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

HRID 839153Notes

Reaction equation

HRID 839153 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

[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. custom[V; Ar is 3,4-methylenedioxyphenyl, R is CH3 ] was prepared from 17.6 g
  2. customaffording 19 g

Sources & evidence

ORD record
ord-4a3352d526254959974bb41f7b09f314
Source dataset
uspto-grants-1978_06
Patent number
US04093736

Reaction notes

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