反应详情

Under nitrogen, 1.5 g (5.6 mmol) of 1-(2-bromocyclopenten-1-yl)-4-(methylthio)benzene (Step 2) was reacted with 1.5 g (11 mmol) of 4-fluorophenylboronic acid (Lancaster) in 30 mL of toluene, 20 mL of ethanol, and 25 mL of 2M Na2CO3 in the presence of 250 mg of Pd(PPh3)4. The reaction was vigorously stirred at reflux overnight and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water, dried (MgSO4), and reconcentrated. Purification by silica gel chromatography with hexane gave 1-[2-(4-fluorophenyl) cyclopenten-1-yl]-4-(methylthio)benzene (41 in Synthetic Scheme X when R5 =SCH3, R10 =F, and R1, R2, R3, R4, R6, R7, R8, R9, R11, and R12 =H) as a colorless solid. mp 46°-47° C.; NMR (CDCl3) d 2.04 (m, J=7 Hz, 2H) , 2.45 (s, 3H), 2.86, (t, J=7 Hz, 4H) , 6.86-6.94 (m, 2H) , 7 . 08 (br s, 4H) , 7.10-7.18 (m, 2H) .

1. temperatureat reflux overnight
2. concentrationconcentrated in vacuo
3. dissolutionThe residue was dissolved in ethyl acetate
4. washwashed with water
5. dry with materialdried (MgSO4)
6. customPurification by silica gel chromatography with hexane