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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 241513Generated: October 29, 2026

Tetrabutylammonium Fluoride → 5-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrrole

https://huagongshe.com/reaction/241513

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactant1,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 23159823—
Reactant4-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzimidic acid methyl esterHCID 66836669—
SolventTetrahydrofuranHCID 8028—
Product5-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-2,4-dihydropyrroleHCID 8669104675%

Reaction Steps

To a solution of 4-bromo-3-methyl-N-trimethylsilanylmethyl-thiobenzimidic acid methyl ester (4.40 g, 13.3 mmol) in dry THF (60 mL) was added 2-(3,5-dichlorophenyl)-1,1,1-trifluoro-2-propene (4.35 g, 16.25 mmol) at −7° C. A solution of tetrabutyl ammoniumfluoride (5.32 mL, 1 M in THF, 5.33 mmol) was added at this temperature and the mixture was allowed to warm to room temperature over night. All volatiles were removed in vacuum. The residue was purified by flash chromatography on silica gel to give the title compound (4.50 g, 75%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08653000B2
Source datasetuspto-grants-2014_02
ORD IDord-008647fd4d7447f2a5e3f27bf0253311
Source noteuspto-grants-2014_02