1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-one → 2-(3,5-Dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide

HRID 62626Notes

Reaction equation

[C:1]1([S:7]([CH2:9]P(=O)(OCC)OCC)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[Cl:24][C:25]1[CH:26]=[C:27]([C:32](=O)[C:33]([F:36])([F:35])[F:34])[CH:28]=[C:29]([Cl:31])[CH:30]=1>C1(C)C=CC=CC=1>[C:1]1([S:7]([CH:9]=[C:32]([C:27]2[CH:28]=[C:29]([Cl:31])[CH:30]=[C:25]([Cl:24])[CH:26]=2)[C:33]([F:36])([F:35])[F:34])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Diethyl [(phenylsulfinyl)methyl]phosphonate (5.00 g, 96% purity, 17.4 mmol) was dissolved in toluene (20 mL) and cooled to 0° C. To the solution potassium tert-butoxide (2.05 g, 18.2 mmol) was added in one portion. This solution was added over 45 minutes to a solution of 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanone (4.26 g, 99% purity, 17.4 mmol) in toluene at 0° C. The reaction mixture was stirred for additional 15 minutes at 0° C. and then warmed to room temperature over 30 minutes. The solution was poured onto hydrochloric acid (3.6%) and the phases were separated. The aqueous phase was extracted with toluene and the combined organic phases were washed with water, dried over sodium sulfate and the solvents evaporated. 2-(3,5-dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide was obtained (6.26 g, 94% purity, 93% yield, E/Z=38/62).

Workup

temperaturewarmed to room temperature over 30 minutes
additionThe solution was poured onto hydrochloric acid (3.6%)
customthe phases were separated
extractionThe aqueous phase was extracted with toluene
washthe combined organic phases were washed with water
dry with materialdried over sodium sulfate
customthe solvents evaporated

Sources & evidence

ORD record: ord-0f1a36e800da48959488e7943f92e231
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447036B2

Reaction notes

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