تفاعل #79649

معادلة التفاعل

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

2-fluorobenzyl bromide

→

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

المردود 55.0%

المذيبات

DMF

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed five times with H2O
2. 2
   تجفيفonce with saturated brine, dried over anhydrous magnesium sulfate
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated
5. 5
   أخرىThe residue was purified by column chromatography on silica gel (elution with gradient methylene chloride/ethyl acetate)

الإجراء التجريبي

40% Methanolic Triton B (2.82 mL, 6.2 mM) was slowly added dropwise to a solution of 5-carbomethoxy-1,2-dihydro-9H-carbazol-4(3H)-one (1.27 g, 5.22 mM) in 10 mL of DMF at 25° C. After 5 minutes, 2-fluorobenzyl bromide (1.19 g, 6.2 mM) was added and the resultant mixture stirred at room temperature for 17 days. The mixture was diluted with ethyl acetate, washed five times with H2O, once with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel (elution with gradient methylene chloride/ethyl acetate) to afford 1.00 g (55%) of the 9-[(2-fluorophenyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one as a tan foam. 1H NMR (DMSO-d6) δ7.7 (dd, 1H, J=1 and 8 Hz), 7.4-7.2 (m, 4H), 7.1 (t, 1H, J=8 Hz), 6.7 (t, 1H, J=8 Hz), 5.65 (s, 2H), 3.8 (s, 3H), 3.0 (t, 2H, J=6 Hz), 2.45 (t, 2H, J=6 Hz), and 2.1 (m, 2H). IR (CDCl3, cm−1) 3050, 2950, 1725, 1652, 1464, 1441, 1288 and 1120. MS (ES) m/e 350, 352.

المصدر