4-(Trifluoromethoxy)benzonitrile

clear light yellow liquid

General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, CuCl (0.05 mol, 5 molpercent), DABCO (0.10 mol, 10 molpercent), 4-HO-TEMPO (0.05 mmol, 5 molpercent) were added. Substrates 1 (1 mmol) and NHGeneral procedure: To a solution of triphenylphosphine oxide (14 mg, 0.050 mmol) in either CHClSynthesis, separation and purification of 1-cyano-4-trifluoromethoxybenzene:4-cyanophenyldiazonium tetrafluoroborate (1 mmol, 1.0 eq) was added to a 50 mL round bottom flask under N2.After sealing with a rubber stopper, 4 ml of deaerated anhydrous acetonitrile was added to the round bottom flask with a syringe, and the reaction flask was stirred under a dry ice bath at -40 °C.Then 0.5 M of AgOCF3 acetonitrile solution (6 ml, 3 mmol, 3.0 eq) was added to the reaction flask with a syringe.The reaction was continued at -40 ° C for 2 hours, and then naturally warmed to room temperature for 13 hours.After completion of the reaction, the reaction solution was extracted twice with 20 ml of dichloromethane, and then the obtained organic phase was dried over anhydrous sodium sulfate.Filtration and rotary distillation under reduced pressure gave a crude product with a small solvent.The crude product is then separated on a silica gel column using a mixture of low boiling petroleum ether: dichloromethane = 20:1.The final product was obtained: 1-cyano-4-trifluoromethoxybenzene as a colorless oily liquid, yield 43percent.4-(Trifluoromethoxy)benzonitrile: To a solution of 1-bromo-4-(trifluoromethoxy)benzene (24 g, 99.6 mmol) in DMF (120 mL) was added CuCN (19.7 g, 200.0 mmol). The reaction mixture was heated at reflux overnight. The reaction mixture was quenched by adding H (7) (1 mmol) was suspended in anhydrous ethanol (0.4 M) and cooled to 0 °C. Dry hydrochloric acid gas was bubbled through the solution for 1 h and the sealed flask was stirred at RT for a further 18 h. The reaction mixture was then concentrated and ether was added. The precipitate was collected, washed with ether and dried in vacuo to give benzimidate hydrochloride 8 (0.74 mmol, 74percent) as a colourless solid; mp 127'128 °C; numax/cm-1 2850, 1642, 1176, 861, 745; deltaH (400 MHz; MeOD) 8.2 (2 H, d, J 8.8 Hz), 7.56 (2 H, d, J 8.8 Hz), 4.68 (2 H, q, J 7.0 Hz), 1.63 (3 H, t, J 7.0 Hz); deltaC (125 MHz; MeOD) 173.4, 155.5, 132.8, 126.0, 123.0, 122.2, 71.7, 13.8; m/z (+ESI) 234 ([M - Cl], 100).General Method For Synthesis of EA12-14 Hydrochlorides To a solution of the appropriate amine intermediate (4 mmol) in methanol (6 ml) was added ethyl 4-iodophenyl imidate hydrochloride (2 mmol). The reaction mixture was stirred over night, solvents evaporated off and the residue purified by crystallization in a mixture of ethanol and ether. EA12 was obtained in 36percent yield, EA13 in 68percent yield and EA 14 in 60percent yield. All compounds were obtained as cream colored solids. EA 12: 1H NMR (DMSO, 300 MHz) delta 3.83 (s, 3H), 4.62 (s, 2H), 6.93-7.36 (m, 4H), 7.59 (d, 2H), 7.96 (d, 2H) and 9.85 (br, N-H); EA 13: 1H NMR (DMSO, 300 MHz) delta 4.77 (s, 2H), 7.35-7.64 (m, 6H), 7.96 (m, 2H) and 10.00 (br, N-H); EA 14: 1H NMR (DMSO, 300 MHz) delta 4.74 (s, 2H), 7.61 (m, 5H), 7.89 (m, 2H) and 9.91 (br, N-H)

Molecular Weight:187.12
XLogP3:2.8
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:187.02449824
Monoisotopic Mass:187.02449824
Topological Polar Surface Area:33
Heavy Atom Count:13
Complexity:209
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes