Dimethyl Sulfoxide → 1-(2-Acetoxyethyl)thio-2-(2,4-difluorophenyl)-1,1-difluoro-2,3-epoxypropane

HRID 1585661Notes

Reaction equation

[H-].[Na+].[CH3:3]S(C)=O.[I-].C[S+](C)(C)=O.[C:13]([O:16][CH2:17][CH2:18][S:19][C:20]([F:32])([F:31])[C:21]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[F:30])=[O:22])(=[O:15])[CH3:14]>C1COCC1>[C:13]([O:16][CH2:17][CH2:18][S:19][C:20]([F:31])([F:32])[C:21]1([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[F:30])[O:22][CH2:3]1)(=[O:15])[CH3:14]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 60% NaH (3.95 g, 0.1 mol) in THF (60 ml)-DMSO (120 ml) was heated to an external temperature of 50° C., followed by the addition of trimethylsulfoxonium iodide (21.7 g, 0.1 mol) in portions. The resulting mixture was stirred for 15 minutes at the same temperature and was then cooled to -20° C. To the reaction mixture, a solution of 2-(2-acetoxyethyl)thio-2,2-difluoro-2',4'-difluoroacetophenone (25.5 g, 0.08 mol) in THE (60 ml) was added dropwise. After being stirred at room temperature for 1.5 hours, the reaction mixture was poured into ice water, followed by extraction with ethyl ether. The ether solution was washed with water, dried over magnesium sulfate and then distilled off under reduced pressure, whereby 1-(2-acetoxyethyl)thio-2-(2,4-difluorophenyl)-1,1-difluoro-2,3-epoxypropane (24.0 g, yield: 90.0%) was obtained as a pale yellow oil.

Workup

temperaturewas then cooled to -20° C
stirringAfter being stirred at room temperature for 1.5 hours
extractionfollowed by extraction with ethyl ether
washThe ether solution was washed with water
dry with materialdried over magnesium sulfate
distillationdistilled off under reduced pressure

Sources & evidence

ORD record: ord-5b66a21faf3c4d109d049328ab5e2b3d
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05939448

Reaction notes

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