Tolylboronic acid → 1,2-Difluoro-4-(4-methylphenyl)-5-[4-(methylsulfonyl)phenyl]benzene

HRID 1839941Notes

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:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>>[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]([CH3:20])=[CH:22][CH:23]=2)=[CH:7][C:6]=1[F:8]

Participants

Reactant 2

HCID 79799Tolylboronic acid

HCID 117919231-Bromo-4,5-difluoro-2-[4-(methylsulfonyl)phenyl]benzene

Product 1

HCID 108322381,2-Difluoro-4-(4-methylphenyl)-5-[4-(methylsulfonyl)phenyl]benzeneYield 97%

Procedure

Following the general procedure outlined in Synthetic Scheme VI, 2.56 g (7.37 mmol) of 1-bromo-4,5-difluoro-2-[(4-methylsulfonyl)phenyl]benzene (Example 18, Step 2) was reacted with 1.35 g (9.93 mmol) of 4-methylphenylboronic acid. Purification by silica gel chromatography (MPLC) with ethyl acetate/hexane (3:7) gave 2.55 g (97%) of 1,2-difluoro-4-(4-methylphenyl)-5-[4-(methylsulfonyl)phenyl]benzene as a colorless solid: mp 147.0-148.0° C.; NMR (CDCl3) δ 2.32 (s, 3H), 3.05 (s, 3H), 6.92 (d, J=8 Hz, 2H), 7.03 (d, J=8 Hz, 2H), 7.17-7.32 (m, 4H), 7.79 (d, J=8 Hz, 2H). MS (FAB): m/e 365 (M+Li). Anal. Calc'd for C20H16F2O2S: C, 67.03; H, 4.50. Found: C, 67.18; H, 4.48.

Workup

customPurification by silica gel chromatography (MPLC) with ethyl acetate/hexane (3:7)

Sources & evidence

ORD record: ord-e78b07cc239e4aa09910c9ba71b3f3bb
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677488B2

Reaction notes

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