m-Chloroperbenzoic acid → 5-bromo-2-(1-hydroxy-1-methylethyl)pyridine N-oxide

HRID 1839150Notes

Reaction equation

HRID 1839150 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[N:6][CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:17].[OH-].[Ca+2].[OH-]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:11])([CH3:9])[CH3:10])=[N+:6]([O-:17])[CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 154863922-(5-Bromopyridin-2-yl)propan-2-ol

Product 1

HCID 227142915-bromo-2-(1-hydroxy-1-methylethyl)pyridine N-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-(1-hydroxy-1-methylethyl) pyridine from Step 1 in methylene chloride (5 ml/mmol) at room temperature was added m-chloroperoxybenzoic acid 70% (1.1 eq) and the resulting mixture was stirred at room temperature for 18 hours. An excess of calcium hydroxide was added and after 5 minutes the mixture was filtered through a bed of celite. The crude product from evaporation of the filtrate was chromatographed on silica gel eluting with 80% ethyl acetate in hexane and the 5-bromo-2-(1-hydroxy-1-methylethyl) pyridine N-oxide compound was obtained as a white solid.

Workup

  1. filtrationwas filtered through a bed of celite
  2. customThe crude product from evaporation of the filtrate
  3. customwas chromatographed on silica gel eluting with 80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-b5425a48d3964ecbbf3865aff40e0baf
Source dataset
uspto-grants-2004_01
Patent number
US06677351B2

Reaction notes

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