تفاعل #57010

معادلة التفاعل

2-(2-Bromo-cyclopent-2-enyl)-ethanol

Na2CO3

2-fluorophenylboronic acid

→

2-[2-(2-fluoro-phenyl)-cyclopent-2-enyl]-ethanol

المذيبات

benzene

EtOH

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with diethyl ether (2×)
2. 2
   تجفيفThe combined organic layers were dried over MgSO4
3. 3
   ترشيحfiltered
4. 4
   أخرىevaporated to dryness
5. 5
   أخرىThe oil was purified by column chromatography on silica gel with 30% EtOAc

الإجراء التجريبي

2-(2-Bromo-cyclopent-2-enyl)-ethanol Intermediate FIVE1 (1.21 g, 6.33 mmol) in benzene (40 mL), and Na2CO3 (7 mL, 2M) was treated with a solution of 2-fluorophenylboronic acid (1.08 g, 7.72 mmol) in EtOH (28 mL). Tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4 (0.38 g, 5 mol %) was added and the mixture was heated to 80° C. for 1.5 h. The mixture was diluted with water and extracted with diethyl ether (2×). The combined organic layers were dried over MgSO4, filtered and evaporated to dryness. The oil was purified by column chromatography on silica gel with 30% EtOAc:hexane to give 2-[2-(2-fluoro-phenyl)-cyclopent-2-enyl]-ethanol Intermediate FIVE2 (1.21 g).

المصدر