76284-63-4

Upstream product

• 85-44-9 phthalic anhydride 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 75-63-8 Bromotrifluoromethane 

Downstream Products

• 1236286-82-0 2,2,2-trifluoro-1-[2-(hydroxymethyl)phenyl]ethanol 
• 1438281-32-3 (±)-3-phenyl-3-(trifluoromethyl)-2-benzofuran-1(3H)-one 

Relevant academic research and scientific papers

Nucleophilic trifluoromethylation of anhydrides employing (trifluoromethyl)trimethylsilane: Synthesis of γ-trifluoromethylated γ-butyrolactones

Fluoride-catalyzed nucleophilic trifluoromethylation of acid anhydrides using CF3SiMe3 provided the corresponding γ-hydroxy-γ- trifluoromethyl-γ-butyrolactones. The utility of these adducts was further demonstrated by treatment with Grignard reagents, lea

Copper(I)-catalyzed trifluoromethylation of phthalic anhydride derivatives with (trifluoromethyl)trimethylsilane

An efficient copper-catalyzed trifluoromethylation of substituted phthalic anhydrides using (trifluoromethyl) trimethylsilane (Me3SiCF 3) as a nucleophilic trifluoromethylating reagent in the presence of 1,10-phenanthroline and KF, followed by quenching the reaction mixture with water has been developed. A possible mechanism was suggested. An efficient copper-mediated trifluoromethylation of substituted phthalic anhydrides using (trifluoromethyl)trimethylsilane (Me3SiCF3) as a nucleophilic trifluoromethylating reagent in the presence of 1,10-phenanthroline and KF, followed by quenching the reaction mixture with water has been developed. A possible mechanism was suggested. Copyright

Trifluoromethylation of carbonyl compounds with sodium trifluoroacetate

In the presence of copper(I) iodide as catalyst, a variety of carbonyl compounds, such as aldehydes, ketones and acid anhydrous, could be trifluoromethylated with sodium trifluoroacetate to give the corresponding alcohols in moderate to high yields, and a possible mechanism was proposed to explain the roles of catalyst and solvent in the reaction system.

Reactions of Trifluoromethyl Bromide and Related Halides: Part 9. Comparison between Additions to Carbonyl Compounds, Enamines, and Sulphur Dioxide in the Presence of Zinc

A Barbier procedure, under moderate pressure, was used for the trifluoromethylation of various carbonyl compounds, starting from trifluoromethyl bromide and zinc in pyridine.Trifluoromethyl methanols were obtained from aldehydes and trifluoromethyl ketones from activated esters.Ethyl benzoate, or acetone, induced the formation of the solvated trifluoromethylzinc derivatives which did not react with carbonyl cpompounds.Consequently, the Barbier condensation in that case was considered to involve nascent organometallics reacting near the zinc surface.The reaction with sulphur dioxide, leading to trifluoromethanesulphinate, showed striking differences from that of carbonyl compounds.It was shown that the main pathway occcured in solution.This condensation was interpreted by the initial formation of sulphur dioxide radical anion, which reacts with trifluoromethyl bromide by a single-electron-transfer process.Attempts to condense iminium salts failed when a hydrogen atom was lacking in the α position.When the iminium ion can be transformed in situ to an enamine, a reaction occured, leading to α-trifluoromethyl ketones.This condensation was interpreted by a chain mechanism involving trifluoromethyl radicals.

REACTIONS OF BROMORTRIFLUOROMETHANE WITH ACID DERIVATIVES IN THE PRESENCE OF ZINC.

Reaction of zinc with bromotrifluoromethane in pyridine gives poorly reactive trifluoromethyl zinc derivatives in the presence of ethyl benzoate whereas the Barbier condensation occurs with activated esters, like ethyl trifluoroacetate or ethyl oxalate, and cyclic anhydrides.