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

HRID 1449210Notes

Reaction equation

HRID 1449210 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-c6e437f434364c6fa0eeb979f31d98e7
Source dataset
uspto-grants-1980_02
Patent number
US04189500

Reaction notes

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