Thiophene-3-boronic acid → 2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-4-(3-thienyl)-3(2H)-furanone

HRID 2298278Notes

Reaction equation

HRID 2298278 reaction equation
Br[C:2]1[C:3](=[O:19])[C:4]([CH3:18])([CH3:17])[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1.[S:20]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21]1>>[CH3:17][C:4]1([CH3:18])[C:3](=[O:19])[C:2]([C:22]2[CH:23]=[CH:24][S:20][CH:21]=2)=[C:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[O:5]1

Participants

3

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 183857274-Bromo-2,2-dimethyl-5-[4-(methylsulfonyl)phenyl]-3(2h)-furanone

Product 1

HCID 117724242,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-4-(3-thienyl)-3(2H)-furanoneYield 5%

Procedure

200 mg of 4-bromo-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone was coupled with 100 mg of thiophene-3-boronic acid according to a procedure similar to the synthetic procedure in Example 2 to yield 10 mg of 2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-4-(3-thienyl)-3(2H)-furanone as a solid. NMR: δ1.56 (s, 6H), 3.09 (s, 3H), 6.92-6.93 (m, 1H), 7.32-7.35 (m, 1H), 7.51-7.52 (m, 1H), 7.90-7.93 (m, 2H), 7.97-8.00 (m, 2H).

Sources & evidence

ORD record
ord-ffff2f86e0d043bdad06b441bee615da
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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