Magnesium Bromide → 5-PHENYLDIPYRROMETHANE

HRID 1794646Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:11]([CH:12]=O)=[CH:10][CH:9]=[CH:8][CH:7]=1.[Mg+2].[Br-].[Br-]>>[CH:8]1[CH:9]=[CH:10][C:11]([CH:6]([C:2]2[NH:1][CH:5]=[CH:4][CH:3]=2)[C:2]2[NH:1][CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:7]=1

Participants

Reactant 2

HCID 82241Magnesium Bromide

HCID 84654086Benzaldehyde, 2-(1H-pyrrol-2-yl)-

Product 1

HCID 43275135-PHENYLDIPYRROMETHANE

Procedure

In the survey of various acid catalysts for the pyrrole-benzaldehyde condensation, MgBr2 gave a good yield of 5-phenyldipyrromethane with little N-confused 5-phenyldipyrromethane and 5,10-diphenyltripyrrane. This observation prompted us to study the effect of MgBr2 on the pyrrole-mesitaldehyde condensation. Four reactions were carried out with 0.1, 0.3, 0.5 or 1.0 equiv of MgBr2 using a 100:1 ratio of pyrrole:mesitaldehyde at room temperature. For the reaction with 0.5 equiv of MgBr2, GC analysis showed 82.9% of 5-mesityldipyrromethane and 0.9% of unreacted mesitaldehyde. Among the acids surveyed, the use of 0.5 equiv of MgBr2 appeared superior for the synthesis of 5-mesityldipyrromethane.

Sources & evidence

ORD record: ord-c343fdbc7c0c4c02958b4a76144b38f6
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022862B2

Reaction notes

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