3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → 2-chloro-1-fluoro-4-[2-(4-methylsulfonylphenyl)phenyl]benzene

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Reaction Steps

Following the general procedure outlined in Synthetic Scheme VI, 6.43 g (20.6 mmol) of 1-bromo-2-[4-(methylsulfonyl)phenyl]benzene (Example 4, Step 2) was reacted with 5.37 g (30.9 mmol) of 3-chloro-4-fluorophenylboronic acid. Purification by silica gel chromatography (Waters Prep-500A) with ethyl acetate/hexane (1:3) gave 6.64 g (89%) of 2-chloro-1-fluoro-4-[2-[4-(methylsulfonyl)phenyl]phenyl]benzene as a colorless solid: mp 179.5-181.1° C.; NMR (CDCl3) δ 3.06 (s, 3H), 6.86-6.93 (m, 1H), 6.98 (t, J=8 Hz, 1H), 7.19 (dd, J=2, 7 Hz, 1H), 7.33 (d, J=8 Hz, 2H), 7.38-7.53 (m, 4H), 7.84 (d, J=9 Hz, 2H). MS (FAB): m/e 367 (M+Li); HRMS Calc'd for C19H14ClFO2S: 360.0387. Found: 360.0401. Anal. Calc'd for C19H14ClFO2S: C, 63.25; H, 3.91; F, 5.27. Found: C, 62.92; H, 4.02; F, 5.19.

Provenance & Evidence