Methanol → 4-Bromo-2-methoxybenzonitrile

Temperatur

55 °C

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).

1. customThe layers were separated
2. washthe organic layer was washed with water (150 mL) and brine (50 mL)
3. dry with materialdried over Mg2SO4
4. filtrationfiltrated
5. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-dfe0619ae872459c9e0030ceb8e4fcb6

Quelldatensatz

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07420066B2