تفاعل #79702

معادلة التفاعل

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

المردود 56.0%

المذيبات

DMF

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with H2O, 1 N HCl, H2O, saturated NaHCO3, H2O, and saturated brine
2. 2
   تجفيفdried over anhydrous magnesium sulfate
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated
5. 5
   أخرىThe residue was purified by column chromatography on silica gel (elution with methylene chloride/ethyl acetate)

الإجراء التجريبي

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.

المصدر