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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 382241Generated: November 2, 2026

Benzene, 1-bromo-4-(trifluoromethyl)- → 3,5-Difluoro-4-methyl-6-(4-trifluoromethylphenyl)-2-(3-trifluoromethylphenoxy)pyridine

https://huagongshe.com/reaction/382241

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzene, 1-bromo-4-(trifluoromethyl)-HCID 67872—
Reactant4-Methyl-2,3,5-trifluoro-6-(3-trifluoromethylphenoxy)pyridineHCID 11301246—
ReactantButyllithiumHCID 178418339—
SolventDiethyl EtherHCID 3283—
Product3,5-Difluoro-4-methyl-6-(4-trifluoromethylphenyl)-2-(3-trifluoromethylphenoxy)pyridineHCID 18752366—

Reaction Conditions

Temperature10 °C

Reaction Steps

Butyl lithium (2.6 ml, 6.6 mmol, 2.5 M solution in hexane) is added to a solution of 1-bromo-4-trifluoromethyl benzene (0.84 ml, 6 mmol) in anhydrous diethyl ether (5 ml) at −30° C. The mixture is stirred for 60 min at −20° C. and for 60 min at 10° C. The solution is allowed to warm to ambient temperature. This solution is then added to a mixture of 4-methyl-2,3,5-trifluoro-6-(3-trifluoromethylphenoxy)pyridine 2A (1.5 g, 5 mmol) in anhydrous diethyl ether (100 ml) at −50° C. during 2.5 hours. The mixture is further stirred for 7 hours at −50° C. and washed with saturated aqueous ammonium chloride and water. After drying and evaporation of the organic layer, the residue is purified by vacuum destillation. One obtains colorless crystals (0.37 g, 0.85 mmol, bp. 130° C. at 0.01-0.02 mbar) of mp. 87° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06310006B1
Source datasetuspto-grants-2001_10
ORD IDord-aa58d48327024eb38f9dfaf2ba6ce417
Source noteuspto-grants-2001_10