m-Chloroperbenzoic acid → 3-(4'-Bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine 1-oxide

HRID 1716289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1716289
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]3[C:17]([O:22][CH3:23])=[N+:18]([O-:32])[CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 685127243-(4'-Bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine

Produkt 1

HCID 685129393-(4'-Bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 3-(4′-bromo-biphenyl-4-yloxymethyl)-2-methoxy-pyridine (0.19 g, 0.51 mmol) from Step B and mCPBA (77% max., 0.25 g, 1.13 mmol) in dichloromethane (5 mL) was stirred at room temperature for 3 days. The reaction was diluted with dichloromethane and washed with aqueous Na2SO3 solution, 1N NaOH solution, water and brine. The organic layer was dried over anhydrous K2CO3 and filtered through Celite. The filtrate was concentrated under vacuo and the residue was purified by chromatography (silica gel, 10% MeOH/EtOAc) to give the desired product. MS: 386, 388 (M+H)+.

Aufarbeitung

  1. washwashed with aqueous Na2SO3 solution, 1N NaOH solution, water and brine
  2. dry with materialThe organic layer was dried over anhydrous K2CO3
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated under vacuo
  5. customthe residue was purified by chromatography (silica gel, 10% MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-35d524410574471fafc78517b49a0945
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803793B2

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