3,4-Dimethylphenylboronic acid → 1,2-Difluoro-4-(3,4-dimethylphenyl)-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 3,4-dimethylphenylboronic acid (step 1) to give 1,2-difluoro-4-(3,4-dimethylphenyl)-5-[4-(methylsulfonyl)phenyl]benzene as a colorless solid: mp 125.1-125.8° C.; NMR (CDCl3) δ 2.16 (s, 3H), 2.23 (s, 3H), 3.04 (s, 3H), 6.69 (dd, J=2, 8 Hz, 1H), 6.86 (S, 1H), 6.95 (d, J=8 Hz, 1H), 7.16-7.26 (m, 3H), 7.29 (d, J=9 Hz, 1H), 7.79 (d, J=9 Hz, 2H); MS (FAB) m/z 379 (M+Li)+; HRMS calc'd for M+ 372.0996, found 372.0978. Anal. calc'd for C20H18F2O2S: C, 67.73; H, 4.87; F, 10.20. Found: C, 67.93; H, 4.92; F, 9.82.

Provenance & Evidence