3-Chloro-4-methoxybenzeneboronic acid → 1-(3-Chloro-4-methoxyphenyl)-4,5-difluoro-2-[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.[Cl:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]>>[Cl:20][C:21]1[CH:22]=[C:23]([C:2]2[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=2[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]Participants
Procedure
Following the general procedure outlined in Synthetic Scheme VI, 4.4 g (13 mmol) of 1-bromo-4,5-difluoro-2-[4-(methylsulfonyl)phenyl]benzene (Step 2) was reacted with 3.1 g (17 mmol) of 3-chloro-4-methoxy phenylboronic acid (Example 5, Step 2). Purification by silica gel chromatography (Waters Prep-500A) with ethyl acetate/hexane (3:7) and subsequent recrystallization from ethyl acetate/hexane gave 4.47 g (95%) of 1-(3-chloro-4-methoxyphenyl)-4,5-difluoro-2-[4-(methylsulfonyl)phenyl]benzene as a colorless solid: mp 147.5°-148.5° C.; NMR (CDCl3) δ 3.05 (s, 3H), 3.88 (s, 3H), 6.75(d, J=9 Hz, 1H), 6.83 (dd, J=2, 9 Hz, 1H), 7.10(d, J=2 Hz, 1H), 7.17-7.32 (m, 4H), 7.83(d, J=9 Hz, 2H). MS (EI): m/e (rel intensity) 408 (33), 314 (15), 294 (52), 279 (63), 251 (100). Anal. Calc'd for C20H15ClF2O3 S.(0.27 ethyl acetate): C, 58.53; H, 3.99; F, 8.79. Found: C, 58.75; H, 3.71; F, 8.52.
Workup
- customPurification by silica gel chromatography (Waters Prep-500A)
- customwith ethyl acetate/hexane (3:7) and subsequent recrystallization from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-209bee424382416e85f152f9f1ee4ab1
- Source dataset
- uspto-grants-1998_04
- Patent number
- US05739166
Reaction notes
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