Bismuth-oxygen → 1-(3-Fluoro-4-methoxyphenyl)-2-[4-(methylthio)phenyl]ethane-1,2-dione

HRID 53846Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:10](=[O:21])[CH:11]([OH:20])[C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Bi]=O>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:10](=[O:21])[C:11]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)=[O:20])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

Conditions

Temperature: 90 °C

Procedure

1-(3-Fluoro-4-methoxyphenyl)-2-hydroxy-2-[4-(methylthio)phenyl]ethanone from step 2 (6.5 mmol, 2.00 g) was diluted with glacial acetic acid (30 mL). Bismuth oxide (11.4 mmol, 5.30 g) was added and the mixture was heated at 90° C. for 2 hours. The crude mixture was filtered through Celite® filter agent, lyophilized and subjected to chromatography, affording the title compound as a yellow solid (642 mg, 32%).

Workup

filtrationThe crude mixture was filtered through Celite®
filtrationfilter agent

Sources & evidence

ORD record: ord-c03c04d544944534b3381d68cd6122e6
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05620999

Reaction notes

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