m-Chloroperbenzoic acid → HCID 67299921, compound

HRID 2368213Notes

Reaction equation

HRID 2368213 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.ClC1C=CC=C(C(OO)=[O:18])C=1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N+:6]([O-:18])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 5200169(5-Bromopyridin-2-yl)methanol

Product 1

HCID 67299921HCID 67299921, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

5-Bromo-pyridin-2-yl-methanol (6.0 g, 31.9 mmol) was dissolved in dichloromethane (80 ml) and cooled to 0° C. A solution of 3-chloroperbenzoic acid (8.26 g, 47.9 mmol) in dichloromethane (20 ml) was slowly added, the ice bath was removed after completion of the addition, and the reaction mixture was stirred at ambient temperature for 1 h. The solvent was removed and the crude product was purified by silica gel chromatography using ethyl acetate to yield 3.68 g (56%) of the title compound.

Workup

  1. customthe ice bath was removed
  2. additionafter completion of the addition
  3. customThe solvent was removed
  4. customthe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4ce3e060ff034c87a4dbc91a7aa5f64e
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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