Dimethyl Sulfoxide → Benzene, 2-fluoro-4-(1-methylethenyl)-1-(trifluoromethyl)-

HRID 1438407Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:14](=O)[CH3:15])[CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11].[CH3:17]S(C)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:3][C:4]1[CH:5]=[C:6]([C:14]([CH3:15])=[CH2:17])[CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 60% sodium hydride (1.96 g, 49.0 mmol) was added DMSO (40 ml) in one portion at 0° C. and the reaction mixture was heated at 80° C. for 40 minutes. After cooling to ambient temperature, to this was added a solution of methyltriphenylphosphonium bromide (17.5 g, 49.0 mmol) in anhydrous DMSO (50 ml) dropwise at 0° C. After being stirred for 1 hour at ambient temperature, to this was added a solution of 1-[3-fluoro-4-(trifluoromethyl)phenyl]ethanone (5.04 g, 24.5 mmol) in anhydrous DMSO (40 ml) dropwise at 0° C. and the reaction was stirred at ambient temperature for 1.5 hours. The mixture was quenched with water (150 ml) and extracted with hexane. The combined solution was washed with water then brine, dried over sodium sulfate and concentrated in vacuo to give the crude title compound (3.20 g containing hexane) as a yellow oil.

Workup

temperatureAfter cooling to ambient temperature
stirringthe reaction was stirred at ambient temperature for 1.5 hours
customThe mixture was quenched with water (150 ml)
extractionextracted with hexane
washThe combined solution was washed with water
dry with materialbrine, dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-652d8e71242b4e8da91c1cf41be1188f
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622589B2

Reaction notes

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