Reaktion #159841

Reaktionsgleichung

NaOH

3-methoxy-6-methyl-2-nitropyridine

NBS

benzoyl peroxide

→

6-(Bromomethyl)-3-methoxy-2-nitropyridine

Lösungsmittel

CCl4

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 56 hours under nitrogen atmosphere
2. 2
   Extraktionextracted
3. 3
   TrocknenThe combined organic layer was dried over Mg2SO4
4. 4
   Filtrationfiltered
5. 5
   SonstigeThe solvent was evaporated
6. 6
   Sonstigeto yield a brown oily

Vorschrift

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.

Quelle