(4-Fluoro-3-methylphenyl)boronic acid → 1,2-Difluoro-4-(4-fluoro-3-methylphenyl)-5-[4-(methylsulfonyl)phenyl]benzene
Reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][C:22]=1[CH3:30]>>[F:9][C:5]1[CH:4]=[C:3]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)[C:2]([C:24]2[CH:25]=[CH:26][C:21]([F:20])=[C:22]([CH3:30])[CH:23]=2)=[CH:7][C:6]=1[F:8]Participants
3
Procedure
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.
Sources & evidence
- ORD record
- ord-e1631433c8dd4afe9547e056ee149c47
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06677488B2
Reaction notes
Loading…