m-Chloroperbenzoic acid → HCID 69065008, compound

HRID 1782090Notes

Reaction equation

HRID 1782090 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[N:10][N:11]([CH3:13])[N:12]=2)=[N:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:22])C=1>ClCCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[N:10][N:11]([CH3:13])[N:12]=2)=[N+:6]([O-:22])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 234386535-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine

Product 1

HCID 69065008HCID 69065008, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine (175 mg, 0.73 mM) and 3-chloroperbenzoic acid (wet, 70%: 0.50 g, 2.05 mM) were dissolved in 1,2-dichloroethane (5 ml) and heated at 80° C. for 1.5 hours. The mixture was submitted directly to silica gel chromatography, eluting with 25% acetonitrile in dichloromethane. 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine 1-oxide was thus obtained as a white solid (165 mg). This material was homogeneous by tlc analysis and was used in the subsequent step without further characterization or purification.

Workup

  1. washeluting with 25% acetonitrile in dichloromethane

Sources & evidence

ORD record
ord-1ec23d976acb4f869970ee250c87a048
Source dataset
uspto-grants-2009_03
Patent number
US07498350B2

Reaction notes

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