4-(Methylthio)phenylboronic acid → 1-Methylsulfanyl-4-[2-(4-methylsulfonylphenyl)-1-cyclopentenyl]benzene

참여 물질

반응 단계

Following a synthetic procedure which was similar to the one outlined in Step 3 of Example 1, 270 mg (0.9 mmol) of 1-(2-bromocyclopenten-1-yl)-4-(methylsulfonyl)benzene (Step 1) was reached with 300 mg (1.8 mmol) of 4-methylthiophenylboronic acid (Example 1, Step 1). Purification by silica gel chromatography (MPLC) with hexane/ethyl acetate (4:1) gave 265 mg (86%) of 1-[2-(4-methylthiophenyl)cyclopenten-1-yl)-4-(methylsulfonyl)benzene as a colorless solid: mp 138°-139° C.; NMR (CDCl3) d 2.08 (m, J=7 Hz, 2H), 2.47 (s, 3H), 2.90 (t, J=7 Hz, 4H), 3.04 (s, 3H), 7.06 (d, J=8 Hz, 2H), 7.11 (d, J=8 Hz, 2H), 7.34 (d, J=8 Hz, 2H), 7.75 (d, J=8 Hz, 2H); ME (EI) m/e (rel intensity) 344 (100), 297 (4), 218 (33); HRMS. Calc'd for C19H20O2S2 : 344.0905. Found: 344.0907. Anal, Calc'd for C19H20O2S2 : C, 66.24; H, 5.85; S, 18.16. Found: C, 66.28; H, 5.81; S, 18.95.

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