1,2-Diphenyl-1-propene → 3-Bromo-1,2-diphenyl-1-propene

HRID 1451501Notes

Reaction equation

HRID 1451501 reaction equation
[C:1]1([CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:16]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.ClC(Cl)(Cl)Cl>[Br:16][CH2:9][C:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[CH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 130701,2-Diphenyl-1-propeneHCID 67184N-bromobutanimide

Product 1

HCID 541245493-Bromo-1,2-diphenyl-1-propeneYield 95.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1,2-diphenyl-1-propene (9.7 g, 50 mmol), N-bromosuccinimide (8.9 g, 50 mmol), dibenzoylperoxide (0.1 g) and tetrachloromethane (50 ml) was heated at reflux for 21 h. The mixture was filtered cold and the solvent evaporated from the filtrate in vacuo to give 13.1 g of 3-bromo-1,2-diphenyl-1-propene as an E/Z isomeric mixture.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 21 h
  3. filtrationThe mixture was filtered cold
  4. customthe solvent evaporated from the filtrate in vacuo

Sources & evidence

ORD record
ord-1ac36d1bcbf54580aebcb1da38c8ed50
Source dataset
uspto-grants-1997_02
Patent number
US05604242

Reaction notes

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