반응 #79710

반응 방정식

methyl 2-chloro-3-nitrobenzoate

2-methoxybenzeneboronic acid

sodium carbonate

→

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

수율 69.5%

용매

THF

aluminum

반응 조건

후처리

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

실험 절차

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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