Phosphorus tribromide → 3-Ethyl-6-(3,4-dimethoxyphenyl)-3-hexenyl bromide

HRID 426863Notes

Reaction equation

HRID 426863 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH:13]([C:15]2([CH2:18][CH3:19])[CH2:17][CH2:16]2)O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P(Br)(Br)[Br:21].[Br-].[Li+]>[Br-].[Zn+2].[Br-]>[CH2:18]([C:15](=[CH:13][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:16][CH2:17][Br:21])[CH3:19]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 82050Lithium BromideHCID 234557662-(3,4-Dimethoxyphenyl)ethyl 1-ethylcyclopropyl carbinol

Product 1

HCID 541546443-Ethyl-6-(3,4-dimethoxyphenyl)-3-hexenyl bromide

Reagents, catalysts & solvents 1

HCID 10421208Zinc bromideCatalyst

Procedure

3-Ethyl-6-(3,4-dimethoxyphenyl)-3-hexenyl bromide [V; Ar is 3,4-(CH3O)2C6H3, R is C2H5 ] was prepared from 16 g. of 2-(3,4-dimethoxyphenyl)ethyl 1-ethylcyclopropyl carbinol (Preparation B4), 16.8 g. of phosphorus tribromide, 16.8 g. of lithium bromide and 17.6 g. of zinc bromide according to the procedure given above in Preparation C1. The product was used directly in the succeeding step (Preparation D4) without isolation.

Sources & evidence

ORD record
ord-16268ad4cefd4d79a3bfaaaf9c1fd43d
Source dataset
uspto-grants-1979_10
Patent number
US04171378

Reaction notes

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