3,4-Dimethylphenylboronic acid → 1,2-Difluoro-4-(3,4-dimethylphenyl)-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.[CH3:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][C:26]=1[CH3:27]>>[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:23]2[CH:24]=[CH:25][C:26]([CH3:27])=[C:21]([CH3:20])[CH:22]=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 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.
Sources & evidence
- ORD record
- ord-8c6cfc042c984a3091aa7b059de7c083
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06677488B2
Reaction notes
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