(4-Fluoro-3-methylphenyl)boronic acid → 1,2-Difluoro-4-(4-fluoro-3-methylphenyl)-5-[4-(methylsulfonyl)phenyl]benzene

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Reaction Steps

Following the general procedure outlined in Synthetic Scheme VI, 1-bromo-4,5-difluoro-2-[4-(methylsulfonyl)phenyl]benzene (Example 18, Step 2) was reacted with 4-fluoro-3-methylphenylboronic acid (Step 1) to give 1,2-difluoro-4-(4-fluoro-3-methylphenyl)-5-[4-(methylsulfonyl)phenyl]benzene as a colorless solid: mp 167.2-167.5° C.; NMR (CDCl3) δ 2.19 (d, J=2 Hz, 3H), 3.04 (s, 3H), 6.71-6.78 (m, 1H), 6.84 (t, J=9 Hz, 1H), 6.92 (dd, J=2, 8 Hz, 1H), 7.18-7.32 (m, 4H), 7.81 (d, J=8 Hz, 2H); MS (FAB) m/z 383 (M+Li)+; HRMS calc'd for M+ 376.0745, found 376.0752. Anal. Calc'd for C20H15F3O2S: C, 63.82; H, 4.02; F, 15.14. Found: C, 64.00; H, 3.95; F, 14.96.

Provenance & Evidence