m-Chloroperbenzoic acid → HCID 67299921, compound

HRID 1260293Notes

Reaction equation

HRID 1260293 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>C(Cl)Cl>[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 methylenechloride (80 ml) and cooled to 0° C. A solution of 3-chloroperbenzoic acid (8.26 g, 47.9 mmol) in methylenechloride (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-95e0ac61ecfe4a9b970e04c13a9930eb
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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