Water → HCID 86631565, compound

HRID 885816Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:26])[CH2:10][C:11]([C:17]2[CH:22]=[C:21]([Br:23])[C:20]([F:24])=[C:19]([Br:25])[CH:18]=2)(O)[C:12]([F:15])([F:14])[F:13])[CH:5]=[CH:6][C:7]=1[CH3:8].S(Cl)(Cl)=O.N1C=CC=CC=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:26])[CH:10]=[C:11]([C:17]2[CH:22]=[C:21]([Br:23])[C:20]([F:24])=[C:19]([Br:25])[CH:18]=2)[C:12]([F:15])([F:14])[F:13])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

Conditions

Temperature: 5 °C

Procedure

To a stirred solution of 1-(3-chloro-4-methylphenyl)-3-(3,5-dibromo-4-fluorophenyl)-4,4,4-trifluoro-3-hydroxy-butan-1-one (1.40 g) in toluene (3 mL) at 80° C. was added thionyl chloride (0.68 g) and pyridine (0.46 g). The mixture was stirred at same temperature for 2 hours. The resulting mixture was then cooled to 5° C. and water (3 mL) was added, and the mixture was allowed to stir and warm to ambient temperature. The layers were separated, and the organic phase was poured into 2N aqueous sodium hydroxide solution (3 mL). After stirring 0.5 hour at room temperature, the organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford the crude title compound as a yellow oil (1.37 g), which was used in the next step without purification.

Workup

stirringto stir
temperaturewarm to ambient temperature
customThe layers were separated
additionthe organic phase was poured into 2N aqueous sodium hydroxide solution (3 mL)
stirringAfter stirring 0.5 hour at room temperature
customthe organic layer was separated
washwashed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-da45876ac39442f6a303d4f3522a4d71
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242283B2

Reaction notes

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