1-Naphthaleneboronic acid → HCID 18385681, compound

HRID 2298276Notes

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.[C:20]1(B(O)O)[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1>>[CH3:17][C:4]1([CH3:18])[C:3](=[O:19])[C:2]([C:28]2[C:29]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:25]=[CH:26][CH:27]=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

Reactant 2

HCID 2545321-Naphthaleneboronic acid

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

Product 1

HCID 18385681HCID 18385681, compound

Procedure

200 mg of 4bromo-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone was coupled with 114 mg of naphthalene-1-boronic acid by a procedure similar to the procedure employed for Example 2 to afford 2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-4-(1-naphthyl)-3(2H)-furanone as a solid. mp: 194-195° C. NMR: δ1.67 (s, 3H), 1.71 (s, 3H), 2.97 (s, 3H), 7.33-7.43 (m, 2H), 7.48-7.60 (m, 2H), 7.51-7.52 (m, 1H), 7.66-7.69 (m, 2H), 7.76-7.78 (m, 2H), 7.90-7.94 (m, 2H), IR (cm−1): 1698, 1404, 1318, 1149, 1092, 772.

Sources & evidence

ORD record: ord-c05e9335b68e42f7a0ea13f21f46bee9
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492416B1

Reaction notes

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