Hydrochloric Acid → 1-(4-Bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-buten-1-one

HRID 645298Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:24])[CH2:9][C:10]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)(O)[C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[CH3:25].S(Cl)(Cl)=O.N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:24])[CH:9]=[C:10]([C:16]2[CH:17]=[C:18]([Cl:23])[CH:19]=[C:20]([Cl:22])[CH:21]=2)[C:11]([F:13])([F:14])[F:12])=[CH:4][C:3]=1[CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 0.3 g of 1-(4-bromo-3-methylphenyl)-3-(3,5-dichlorophenyl)-3-hydroxy-4,4,4-trifluorobutane-1-one synthesized under Synthetic Example 1 in 3 g toluene, 0.391 g of thionyl chloride and 0.104 g of pyridine were added at room temperature and the mixture was stirred for 1 hour at 80° C. After the end of reaction, the reaction solution was cooled to room temperature, added with toluene and 2N hydrochloric acid and separated, and then an organic layer was washed with water and dried with anhydrous magnesium sulfate to distill off the solvent under reduced pressure. The resulting residue, which although contains mixed geometrical isomers, was purified using silica gel column chromatography that was eluted with ethyl acetate-hexane (1:10), and 0.244 g of aimed product was obtained as yellow solid.

Workup

customAfter the end of reaction
temperaturethe reaction solution was cooled to room temperature
customseparated
washan organic layer was washed with water
dry with materialdried with anhydrous magnesium sulfate
distillationto distill off the solvent under reduced pressure
additionThe resulting residue, which although contains mixed geometrical isomers
customwas purified
washwas eluted with ethyl acetate-hexane (1:10)

Sources & evidence

ORD record: ord-e22aed4b04c84b249e30a302909ddcc8
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700808B2

Reaction notes

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