m-Chloroperbenzoic acid → HCID 117667333, compound

HRID 712780Notes

Reaction equation

HRID 712780 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8][S:9][CH3:10])[CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:16]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8][S:9]([CH3:10])=[O:16])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68756332HCID 68756332, compound

Product 1

HCID 117667333HCID 117667333, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromo-5-methylsulfanylmethyl-pyridine (6.0 g, 28 mmol) is dissolved in chloroform (200 mL) and the solution is cooled to 0° C. Meta-chloroperoxybenzoic acid (7.2 g, 30 mmol, 72%) is added slowly at 0° C. and the reaction mixture is stirred at 0° C. for 1 hr. Then the solvent is removed and the residue is purified by flash column chromatography to give 3.5 g of 3-bromo-5-methanesulfinylmethyl-pyridine.

Workup

  1. customThen the solvent is removed
  2. customthe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-396e66f25b88460788ff127229990f42
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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