3,5-Dibromopyridine → 3,5-Dibromopyridine 1-oxide

HRID 917618Notes

Reaction equation

HRID 917618 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.ClC1C=CC=C(C(OO)=[O:17])C=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N+:4]([O-:17])[CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

4

Reactant 2

HCID 693693,5-DibromopyridineHCID 70297m-Chloroperbenzoic acid2×

Product 1

HCID 6200033,5-Dibromopyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,5-Dibromopyridine 2.37 g is dissolved in methylene chloride 25 ml and thereto is added m-chloroperbenzoic acid 2.96 g at room temperature under stirring. After stirring for 5 hours at room temperature, additional m-chloroperbenzoic acid 246 mg is added thereto and the mixture is stirred. After 15 hours the solvent is removed in vacuo and the residue is purified by silica gel chromatography (solvent; n-hexane:ethyl acetate=1:1) to give 3,5-dibromopyridine N-oxide as colorless crystals, 2.26 g. mp 140-142° C.

Workup

  1. stirringAfter stirring for 5 hours at room temperature
  2. stirringthe mixture is stirred
  3. customAfter 15 hours the solvent is removed in vacuo
  4. customthe residue is purified by silica gel chromatography (solvent; n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-4588c7ebedeb496eb9089a9308afeb58
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

Loading…