Trifluoromethyl benzoates

Flutolanil and its metabolites containing the 2-(trifluoromethyl)benzanilide moiety are converted to methyl 2-(trifluoromethyl)benzoate (2-TFBA Me-ester) by alkaline hydrolysis and methylation for GC/MS analyses. 

PHOTOINDUCED ELECTRON-TRANSFER DEOXYGENATION OF BENZOATES AND m-(TRIFLUOROMETHYL)BENZOATES WITH 9-ETHYL-3.6-DIMETHYLCARBAZOLE... 

Tribenzoyl-2-0[(3-trifluoromethyl)benzoyl]-a-D-ribofuranose a-D-Ribofuranose, 1,3,5-tribenzoate 2-[3-(trifluoromethyl)benzoate (13) (145828-13-3)... 

Bis(trifluoromethyl)benzoyl chloride (0.64mmol) was added to 8-phenyl-l,4-dioxaspiro[4.5]-decane-8-methanol (0.6 mmol) dissolved in 3 ml CH2C12 and the mixture stirred 16 hours at ambient temperature. The solution was then treated with triethylamine (0.6 mmol) and 4-dimethylamino pyridine (1 crystal), then stirred 1 hour at ambient temperature. The mixture was then retreated with 3,5-bis(trifluoromethyl)benzoyl chloride (0.32 mmol), then stirred additional 1 hour, and diluted with 10 ml water. The solution was extracted three times with 10 ml CH2C12 and combined fractions washed with brine, dried with MgS04, and concentrated. The residue was purified by flash chromatography with silica gel using isohexane/EtOAc, 5 1, and the product isolated in 78% yield as a colorless oil contaminated with about 10% (4-oxo-l-phenylcyclohexyl)-methyl 3,5-bis(trifluoromethyl)benzoate. 

Preparation of l-([4-[4-fluorophenyl]piperidin-l-yl]-l-phenylcyclohexane)-methyl 3,5-bis(trifluoromethyl)benzoate... 

Prudhomme, D. R., Wang, Z., Rizzo, C. J. An Improved Photosensitizer for the Photoinduced Electron-Transfer Deoxygenation of Benzoates and m-(Trifluoromethyl)benzoates. J. Org. Chem. 1997, 62, 8257-8260. 

SENSITIZERS AP = acetophenone BP = benzophenone A = acetone B = methyl 3,5-bis(trifluoromethyl)benzoate C = (-)-tetrabomyl 1,2,4,5-benzene tetracarboxylate D = (-)-hexakis(l-methylheptyl) benzenehexacarboxylate MB = methyl benzoate P = phenan-threne CNN = 1-cyanonaphthalene DCA = 9,10-dicyanoanthracene DCB = 1,4-dicyano-benzene DCN = 1,4-dicyanonaphthalene CuOTf = copper trifluoromethanesulfonate benzene complex TPT = tetraphenylpyrylium tetrafluoroborat. 

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