Reaktion #57509

Reaktionsgleichung

methylene chloride

4-bromo-2-fluoro-benzonitrile

methanol

potassium carbonate

→

4-bromo-2-methoxy-benzonitrile

Ausbeute 95.6%

Lösungsmittel

DMF

water

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe layers were separated
2. 2
   Waschenthe organic layer was washed with water (150 mL) and brine (50 mL)
3. 3
   Trocknendried over Mg2SO4
4. 4
   Filtrationfiltrated
5. 5
   Einengenconcentrated under reduced pressure

Vorschrift

A mixture of 4-bromo-2-fluoro-benzonitrile (15.0 g, 75.0 mmol), methanol (30.4 mL, 350 mmol) and potassium carbonate (31.1 g, 225 mmol) in DMF (150 mL) was stirred under argon at 55° C. overnight. At this point TLC (100% methylene chloride) revealed no starting material, and the reaction mixture was poured into ether (300 mL) and water (150 mL). The layers were separated, and the organic layer was washed with water (150 mL) and brine (50 mL), dried over Mg2SO4, filtrated, and concentrated under reduced pressure, providing (15.2 g, 95.5%) of 4-bromo-2-methoxy-benzonitrile as a white solid. 1H-NMR (CDCl3) δ 7.41 (d, J=8.1 Hz, 1H), 7.16 (dd, J=8.1, 1.6 Hz, 1H), 7.13 (d, J=1.6 Hz, 1H), 3.93 (s, 3H); MS GC-MS (M+=211; RT=6.15 min).

Quelle