Reacción #79710

Ecuación de reacción

methyl 2-chloro-3-nitrobenzoate

2-methoxybenzeneboronic acid

sodium carbonate

→

2-carbomethoxy-6-nitro-2′-methoxy-biphenyl

Rendimiento 69.5%

Disolventes

THF

aluminum

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 27 hours
2. 2
   OtroThe THF was removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate
4. 4
   LavadoThe mixture was washed with with H2O, 1 N HCl, H2O, sat. NaHCO3, and saturated brine
5. 5
   Secadodried over magnesium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe resultant light brown oil was purified by column chromatography on silica (elution with gradient toluene/ethyl acetate)

Procedimiento

A solution of methyl 2-chloro-3-nitrobenzoate (2.16 g, 10.0 mM), 2-methoxybenzeneboronic acid (1.64 g, 10.5 mM), tetrakis(triphenylphosphine)palladium (0) (584 mg, 0.5 mM), and 2 M aqueous sodium carbonate (10.5 mL, 21.0 mM) in 50 mL of THF was wrapped in aluminum foil and stirred at reflux for 27 hours. The THF was removed in vacuo and the residue dissolved in ethyl acetate. The mixture was washed with with H2O, 1 N HCl, H2O, sat. NaHCO3, and saturated brine, dried over magnesium sulfate, filtered, and concentrated. The resultant light brown oil was purified by column chromatography on silica (elution with gradient toluene/ethyl acetate) to afford 2.0 g (69%) of 2-carbomethoxy-6-nitro-2′-methoxy-biphenyl as a yellow-orange solid. 1H NMR (CDCl3) δ8.05 (d, 1H, J=8 Hz), 7.95 (d, 1H, J=8 Hz), 7.55 (t, 1H, J=8 Hz), 7.35 (t, 1H, J=8 Hz), 7.05 (d, 1H, J=8 Hz), 7.0 (t, 1H, J=8 Hz), 6.9 (d, 1H, J=8 Hz), 3.7 (s, 3H), and 3.6 (s, 3H). IR (KBr, cm−1) 1730, 1538, 1499, 1366, 1298, 1271, 1130, 774, 765, 759, 752, and 707. MS (ES) m/e 288.

Fuente