3-Bromopyridine-4-carboxaldehyde → 3-Bromo-4-(prop-1-en-1-yl)pyridine

HRID 2390147Notes

Reaction equation

HRID 2390147 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[CH:9][CH2:10]CCC.BrC1C=NC=CC=1C=O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[CH:9][CH3:10]

Participants

4

Reactant 2

HCID 27629973-Bromopyridine-4-carboxaldehydeHCID 670080793-Bromo-4-(hex-1-en-1-yl)pyridine

Product 1

HCID 670080873-Bromo-4-(prop-1-en-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst

Procedure

Following the general method as outlined in Intermediate 12, starting from 3-bromo-4-pyridinecarboxaldehyde (Aldrich) and ethyltriphenylphosphonium bromide, the title compound (mixture of cis and trans isomers) was obtained as a colorless liquid after purification by flash column chromatography, eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-8b3bb53a700c4aa598605a96d7668fee
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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