Reaktion #79710

Reaktionsgleichung

methyl 2-chloro-3-nitrobenzoate

2-methoxybenzeneboronic acid

sodium carbonate

→

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

Ausbeute 69.5%

Lösungsmittel

THF

aluminum

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

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