m-Chloroperbenzoic acid → HCID 22714295, compound

HRID 351740

Reaction equation

HRID 351740 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:17].[OH-].[Ca+2].[OH-]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[N+:4]([O-:17])[CH:5]=[C:6]([C:8]([OH:11])([CH3:9])[CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 223919662-(5-Bromo-3-pyridyl)propan-2-ol

Product 1

HCID 22714295HCID 22714295, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-bromo-5-(1-hydroxy-1-methylethyl)pyridine from Step 1 (3.1 mmol) in chloroform (10 mL) was added m-chloroperoxybenzoic acid 70% (1.5 eq) and the resulting mixture was stirred at room temperature for 18 hours. An excess of calcium hydroxide was added and after stirring for 5 minutes, the mixture was filtered through celite and the filtrate was evaporated. The crude material was chromatographed on silica gel eluting with 10% ethanol in methylene chloride (saturated with ammonia) to afford the 3-bromo-5-(1-hydroxy-1-methylethyl)pyridine-N-oxide compound as a solid.

Workup

  1. stirringafter stirring for 5 minutes
  2. filtrationthe mixture was filtered through celite
  3. customthe filtrate was evaporated
  4. customThe crude material was chromatographed on silica gel eluting with 10% ethanol in methylene chloride (saturated with ammonia)

Sources & evidence

ORD record
ord-5084663d34d84e07a461dca7efbaf530
Source dataset
uspto-grants-2004_06
Patent number
US06743802B2

Linked notes

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