m-Chloroperbenzoic acid → 3-(benzyloxy)-5-bromopyridine N-oxide

HRID 1259089

Reaktionsgleichung

Reaktionsgleichung von HRID 1259089
[CH2:1]([O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:24])C=1>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[N+:11]([O-:24])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 153891983-(Benzyloxy)-5-bromopyridine

Produkt 1

HCID 582134893-(benzyloxy)-5-bromopyridine N-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 3-(benzyloxy)-5-bromopyridine (from step 1) (1.0 eq.) and meta-chloroperbenzoic acid (mCPBA) (4.0 eq.) in dichloromethane (0.1 M) was stirred at room temperature for 18 hours. The reaction was quenched with saturated aqueous NaHCO3 solution and extracted with dichloromethane three times. The combined organic layers were dried over anhydrous MgSO4 and concentrated en vacuo. The crude residue was purified by a COMBIFLASH® system (ISCO) using 0-100% ethyl acetate in hexane to give 3-(benzyloxy)-5-bromopyridine 1-oxide.

Aufarbeitung

  1. customThe reaction was quenched with saturated aqueous NaHCO3 solution
  2. extractionextracted with dichloromethane three times
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. concentrationconcentrated en vacuo
  5. customThe crude residue was purified by a COMBIFLASH® system (ISCO)

Quellen und Nachweise

ORD-Eintrag
ord-ffcc0f99ca19412cb283d8b33d0bbc84
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466167B2

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