2-Chlorophenylboronic acid → 5-(2-Chlorophenyl)-4-cyano-3-nitroanisole

5-Bromo-4-cyano-3-nitroanisole [prepared by the method of Harrison el al, J.Chem.Soc.C, 1769 (1966)] (250 mg, 0.86 mmol) and 2-chlorophenylboronic acid (150 mg, 0.96 mmol) were dissolved in a mixture of toluene (10 ml), EtOH (5.6 ml), and 1N aqueous sodium carbonate (1.7 ml). The solution was placed under a nitrogen atmosphere and tetrakis(triphenylphosphine)palladium (30 mg, 0.03 mmol) added. After refluxing for 3 h, the solvent was removed from the reaction mixture under reduced pressure. The residue was partitioned between H2O (50 ml) and EtOAc (50 ml) and the EtOAc layer washed with H2O (2×50 ml), and dried over MgSO4. Following removal of the solvent, the crude material was purified on silica gel, eluting with hexane/ether (1/1, v/v). This gave the subtitle compound as a colourless gum (252 mg, 100%). Rf 0.38 (hexanelether 1:1, v/v). MS m/z 306 and 308 (MNH4+).

1. temperatureAfter refluxing for 3 h
2. customthe solvent was removed from the reaction mixture under reduced pressure
3. customThe residue was partitioned between H2O (50 ml) and EtOAc (50 ml)
4. washthe EtOAc layer washed with H2O (2×50 ml)
5. dry with materialdried over MgSO4
6. customremoval of the solvent
7. customthe crude material was purified on silica gel
8. washeluting with hexane/ether (1/1

ORD-Eintrag

ord-cebba33b7a7f4a7e9df9191ae0718503

Quelldatensatz

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06103738