반응 #65797

반응 방정식

1-(2-bromocyclopenten-1-yl)-4-(methylthio)benzene

4-fluorophenylboronic acid

Na2CO3

→

1-[2-(4-fluorophenyl)cyclopenten-1-yl]-4-(methylthio)benzene

용매

toluene

ethanol

반응 조건

후처리

1. 1
   온도at reflux overnight
2. 2
   농축concentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
4. 4
   세척washed with water
5. 5
   건조dried (MgSO4)
6. 6
   기타Purification by silica gel chromatography with hexane

실험 절차

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).

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