Benzoyl Peroxide → 3-Methoxy-2-nitro-6-pyridylmethyl bromide

HRID 72659

Reaktionsgleichung

Reaktionsgleichung von HRID 72659
[CH3:1][O:2][C:3]1[C:4]([N+:10]([O-:12])=[O:11])=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1.C1C(=O)N([Br:20])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[OH-].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:9][C:6]1[N:5]=[C:4]([N+:10]([O-:12])=[O:11])[C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Komponenten

6

Edukt 4

HCID 7187Benzoyl PeroxideHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 27279653-Methoxy-6-methyl-2-nitropyridine

Produkt 1

HCID 144051243-Methoxy-2-nitro-6-pyridylmethyl bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 3-methoxy-6-methyl-2-nitropyridine (10.08 g, 60 mmol), NBS (9.79 g, 55 mmol), and benzoyl peroxide (2 g, 6 mmol) in CCl4 (250 mL) was refluxed for 56 hours under nitrogen atmosphere. The reaction mixture was added 100 mL 1M NaOH aq. and extracted using ethyl acetate (3×300 mL). The combined organic layer was dried over Mg2SO4 and filtered. The solvent was evaporated to yield a brown oily. 1H-NMR (CDCl3): δ 3.99 (s, 3H, OCH3), 4.51 (s, 2H, CH2), 7.55 (d, 1H, J=8.8 Hz, Py-H), 7.70 (d, 1H, J=8.4 Hz, Py-H). HR-MS (ESI+) m/z 246.9600 [M+1]+ C7H7BrN2O3 requires 245.9640.

Aufarbeitung

  1. temperaturewas refluxed for 56 hours under nitrogen atmosphere
  2. extractionextracted
  3. dry with materialThe combined organic layer was dried over Mg2SO4
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. customto yield a brown oily

Quellen und Nachweise

ORD-Eintrag
ord-836af7366fa74fcda1241520e5f003c4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829003B2

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