(2H-1,3-benzodioxol-5-yl)boronic acid → 5-[4,5-Difluoro-2-[4-(methylsulfonyl)phenyl]phenyl]-1,3-benzodioxole

HRID 1839942Notes

Reaction equation

HRID 1839942 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.[O:20]1[C:24]2[CH:25]=[CH:26][C:27](B(O)O)=[CH:28][C:23]=2[O:22][CH2:21]1>>[F:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([C:27]2[CH:26]=[CH:25][C:24]3[O:20][CH2:21][O:22][C:23]=3[CH:28]=2)=[C:3]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)[CH:4]=1

Participants

3

Reactant 2

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 117919231-Bromo-4,5-difluoro-2-[4-(methylsulfonyl)phenyl]benzene

Product 1

HCID 105004665-[4,5-Difluoro-2-[4-(methylsulfonyl)phenyl]phenyl]-1,3-benzodioxoleYield 99%

Procedure

Following the general procedure outlined in Synthetic Scheme I, 2.24 g (6.45 mmol) of 1-bromo-4,5-difluoro-2-[4-(methylsulfonyl)phenyl]benzene (Example 18, Step 2) was reacted with 1.39 g (8.38 mmol) of (1,3-benzodioxol-5-yl)boronic acid (Step 1). Purification by silica gel chromatography (MPLC) with ethyl acetate/hexane (1:4) gave 2.47 g (99%) of 5-[4,5-difluoro-2-[4-(methylsulfonyl)phenyl]phenyl]-1,3-benzodioxole as a colorless solid: mp 110.0-111.0° C.; NMR (CDCl3) δ 3.05 (s, 3H), 5.95 (s, 2H), 6.47-6.52 (m, 2H), 6.67 (d, J=8.5 Hz, 1H),-7.16-7.24 (m, 2H), 7.32 (d, J=8.5 Hz, 2H), 7.82 (d, J=8.5 Hz, 2H). MS (FAB): m/e 395 (M+Li). Anal. Calc'd for C20H14F2O4S: C, 61.85; H, 3.63. Found: C, 61.92; H, 3.66.

Workup

  1. customPurification by silica gel chromatography (MPLC) with ethyl acetate/hexane (1:4)

Sources & evidence

ORD record
ord-0a0f7e311a82498e8739c2b3b006c58f
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

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