Sulfuric Acid → 5-Bromo-2-(1-methylvinyl)pyridine N-oxide

HRID 971118Notes

Reaction equation

HRID 971118 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9](O)([CH3:11])[CH3:10])=[N+:6]([O-:8])[CH:7]=1.S(=O)(=O)(O)O.[OH-].[Na+]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([CH3:11])=[CH2:10])=[N+:6]([O-:8])[CH:7]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 227142915-bromo-2-(1-hydroxy-1-methylethyl)pyridine N-oxide

Product 1

HCID 694123775-Bromo-2-(1-methylvinyl)pyridine N-oxide

Conditions

Temperature
130 °C

Procedure

A mixture of 5-bromo-2-(1-hydroxy-1-methylethyl)pirydine N-oxide from step 2 of example 30 (1.29 g) and 25% aqueous sulfuric acid was heated at 130° C. for 2 days. After cooling, the mixture was made slightly basic using 10N aqueous sodium hydroxide and partitioned between ethyl acetate and water. The crude product from evaporation of the organic phase was used as such in step 2.

Workup

  1. temperatureAfter cooling
  2. custompartitioned between ethyl acetate and water
  3. customThe crude product from evaporation of the organic phase

Sources & evidence

ORD record
ord-041e5dc1eab34647a6a82cfe66f88f83
Source dataset
uspto-grants-2007_12
Patent number
US07312334B2

Reaction notes

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