3,5-Bis(trifluoromethyl)benzonitrile

colorless to light yellow liquid

Into a 2-L three-necked flask, were charged 300 g (1.17 mol) of 3, 5-bis(trifluoromethyl)benzamide obtained in the same manner as in Example 7, 183.6 g (0.7 mol) of triphenylphosphine, 107.7 g (0.7 mol) of carbon tetrachloride and 400 ml of tetrahydrofuran. General procedure: To a solution of the aldoxime or the amide (1.0 mmol) and Et3N (1.5mmol) in EtOAc (1 mL, 1 M) at r.t. was added XtalFluor-E8 (1.1 mmol)portionwise over ca. 2 min. The resulting solution was stirred at r.t.for 1 h. The reaction mixture was quenched with sat. aq Na2CO3 and extracted with CH2Cl2 (2 × 10 mL). The combined organic layers were washed with H2O and brine, dried (MgSO4), and concentrated under vacuum to afford the crude nitrile, which was purified by flash chromatography, if required.General procedure: A mixture of copper salt (0.3 mmol) and 2 (0.8 mmol) in DMF (2 mL)was stirred at room temperature under a dry nitrogen atmospherefor 10 min to give a homogeneous solution. Next the aryl bromide(1 mmol), base (1.0 mmol), KI (0.5 mmol), K4Fe(CN)6 (0.22 mmol)and DMF (2 mL) were added and the mixture stirred at 130 °C for 10 h(Table 2). After completion (as monitored by TLC), H2O (15 mL) was added and the organic layer was extracted with EtOAc (3 × 15 mL), washed with brine (15 mL), dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by columnchromatography. All the products are known and were characterisedby IR, NMR and melting points and their spectroscopic data identicalto that reported in the literature.In an autoclave, 1 equiv. of aryl halide or heteroaryl halide, 2 equiv. of 1-alkylimidazole, 0.1 equiv. of CuI, 0.2 equiv. of dried K4[Fe(CN)6] (potassium hexacyanoferrate(II)), tetradecane as an internal standard for the GC analysis and a suitable amount of toluene were combined under argon and heated to 160 C. (The K4[Fe(CN)6] was dried by heating powdered K4[Fe(CN)6]x3H2O in a vacuum of 1 mbar to 80 C. for at least 24 hours.) After 16 hours, the reaction mixture was cooled to room temperature. Conversion and yield were determinable by means of gas chromatography. An isolation of the product took place according to the customary workup (distillation, crystallization or chromatography).In an autoclave, 1 equiv. of aryl halide or heteroaryl halide, 2 equiv. of 1-alkylimidazole, 0.1 equiv. of CuI, 0.2 equiv. of dried K4[Fe(CN)6] (potassium hexacyanoferrate(II)), tetradecane as an internal standard for the GC analysis and a suitable amount of toluene were combined under argon and heated to 160 C. (The K4[Fe(CN)6] was dried by heating powdered K4[Fe(CN)6]x3H2O in a vacuum of 1 mbar to 80 C. for at least 24 hours.) After 16 hours, the reaction mixture was cooled to room temperature. Conversion and yield were determinable by means of gas chromatography. An isolation of the product took place according to the customary workup (distillation, crystallization or chromatography).In an autoclave, 1 equiv. of aryl halide or heteroaryl halide, 2 equiv. of 1-alkylimidazole, 0.1 equiv. of CuI, 0.2 equiv. of dried K4[Fe(CN)6] (potassium hexacyanoferrate(II)), tetradecane as an internal standard for the GC analysis and a suitable amount of toluene were combined under argon and heated to 160 C. (The K4[Fe(CN)6] was dried by heating powdered K4[Fe(CN)6]x3H2O in a vacuum of 1 mbar to 80 C. for at least 24 hours.) After 16 hours, the reaction mixture was cooled to room temperature. Conversion and yield were determinable by means of gas chromatography. An isolation of the product took place according to the customary workup (distillation, crystallization or chromatography).

Used as an intermediate in organic synthesis

Molecular Weight:239.12
XLogP3:4
Hydrogen Bond Acceptor Count:7
Exact Mass:239.01696807
Monoisotopic Mass:239.01696807
Topological Polar Surface Area:23.8
Heavy Atom Count:16
Complexity:273
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes