m-Chloroperbenzoic acid → HCID 67299921, compound

HRID 467616Notes

Reaction equation

HRID 467616 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-64224fedb05144baa1094ab08980c7a3
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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