(4-Chloro-3-methylphenyl)boronic acid → HCID 10572620, compound

HRID 1839947Notes

Reaction equation

HRID 1839947 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:26]=[CH:25][C:24](B(O)O)=[CH:23][C:22]=1[CH3:30]>>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[C:3]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=3)=[CH:4][C:5]([F:9])=[C:6]([F:8])[CH:7]=2)=[CH:23][C:22]=1[CH3:30]

Participants

3

Reactant 2

HCID 3786632(4-Chloro-3-methylphenyl)boronic acidHCID 117919231-Bromo-4,5-difluoro-2-[4-(methylsulfonyl)phenyl]benzene

Product 1

HCID 10572620HCID 10572620, compound

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-chloro-3-methylphenylboronic acid (Step 1) to give 4-(4-chloro-3-methylphenyl)-1,2-difluoro-5-[4-(methylsulfonyl)phenyl]benzene as a colorless solid: mp 151.5-152.2° C.; NMR (CDCl3) δ 2.29 (s, 3H), 3.05 (s, 3H), 6.73 (dd, J=2, 8 Hz, 1H), 6.98 (d, J=2 Hz, 2H), 7.16 (d, J=9 Hz, 1H), 7.19-7.32 (m, 4H), 7.82 (d, J=9 Hz, 2H); MS (FAB) m/z 399 (M+Li)+; HRMS calc'd for M+ 392.0449, found 392.0437. Anal. Calc'd for C20H15ClF2O2S: C, 61.15; H, 3.85; F, 9.67. Found: C, 61.04; H, 3.79; F, 9.55.

Sources & evidence

ORD record
ord-e00f9d4834c94092a147c571b30f8eda
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

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