3-Fluoro-4-methoxyphenylboronic acid → HCID 10546170, compound

Participants

Reaction Steps

Following the general procedure outlined in Synthetic Scheme VI, 5.0 g (16 mmol) of 1-bromo-2-[4-(methylsulfonyl)phenyl]benzene (Step 2) was reacted with 4.1 g (24 mmol) of 3-fluoro-4-methoxyphenylboronic acid (Step 3). Purification by silica gel chromatography (Waters Prep-500A) with ethyl acetate/hexane (35:65) and subsequent recrystallization from ethyl acetate/hexane gave 4.82 g (88%) of 2-fluoro-1-methoxy-4-[2-[4-(methylsulfonyl)phenyl]phenyl]benzene as a colorless solid: mp 136.2-136.6° C.; NMR (CDCl3) δ 3.06 (s, 3H), 3.87 (s, 3H), 6.72-6.89 (m, 3H), 7.31-7.51 (m, 6H), 7.81 (d, J=9 Hz, 2H). MS (EI): m/e (rel intensity) 356 (100), 262 (28), 246 (22); HRMS Calc'd for C20H17FO3S: 356.0882. Found: 356.0881. Anal. Calc'd for C20H17FO3S: C, 67.40; H, 4.81; F, 5.33. Found: C, 67.24; H, 4.83; F, 5.25.

Provenance & Evidence