반응 #79702

반응 방정식

5-carbomethoxy-1,2-dihydro-9H-carbazol-4(3H)-one

a-bromo-2,6-dichlorotoluene

potassium carbonate

→

9-[(2,6-dichlorophenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one

수율 56.0%

용매

DMF

ethyl acetate

반응 조건

후처리

1. 1
   세척washed with H2O, 1 N HCl, H2O, saturated NaHCO3, H2O, and saturated brine
2. 2
   건조dried over anhydrous magnesium sulfate
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타The residue was purified by column chromatography on silica gel (elution with methylene chloride/ethyl acetate)

실험 절차

A suspension of 5-carbomethoxy-1,2-dihydro-9H-carbazol-4(3H)-one (973 mg, 4.0 mM), a-bromo-2,6-dichlorotoluene (1.19 g, 4.8 mM), and potassium carbonate (553 mg, 4.0 mM) in 10 mL DMF was stirred at room temperature for 24 hours. The mixture was diluted with ethyl acetate, washed with H2O, 1 N HCl, H2O, saturated NaHCO3, H2O, and saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated. The residue was purified by column chromatography on silica gel (elution with methylene chloride/ethyl acetate) to afford 900 mg (56%) of the 9-[(2,6-dichlorophenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one as a white foam. 1H NMR (CDCl3) δ7.4-7.2 (m, 6H), 5.6 (s, 2H), 4.0 (s, 3H), 2.9 (t, 2H, J=6 Hz), 2.55 (t, 2H, J=6 Hz), and 2.2 (m, 2H). IR (KBr, cm−1) 1725 and 1652. MS (ES) m/e 400, 402, 404.

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