2,2,2-Trifluoro-1-(3-nitrophenyl)ethanone

2, 2, 2-trifluoroacetophenone (0.5 mL, 3.68 mmol) was dissolved in sulfuric acid (3 mL), and added with NaN02, 2, 2-trifluoroacetophenone (0.5 mL, 3.68 mmol) was dissolved in sulfuric acid (3 mL), and added with NaNOExample 148A2, 2, 2-trifluoro-1-(3-nitrophenyl)ethanone; 20.0 g (114.9 mmol) of 2, 2, 2-trifluoroacetophenone were initially charged in 80 ml of conc. sulphuric acid, and the mixture was cooled to -10° C. A solution, prepared beforehand at -10° C., of 4.8 ml (114.8 mmol) of nitric acid in 20 ml of conc. sulphuric acid was added dropwise to this mixture such that the reaction temperature did not exceed -5° C. After the addition had ended, the reaction mixture was stirred between -10° C. and 0° C. for 1 h and then added carefully to ice-water. By addition of 50percent strength aqueous sodium hydroxide solution, the pH of the mixture was adjusted to about 9-10. The mixture was extracted three times with ethyl acetate, and the combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase initially cyclohexane/dichloromethane 2:1 to 1:1, finally pure dichloromethane) This gave 19.2 g of the target product (76.2percent of theory).LC-MS (Method 6): Ro a solution of 2, 2, 2-trifluoro-1 -phenylethan-1 -one (5 g, 28.7 mmol) in C.H2SO4 (10 mL) at -5 °C was added a solution of c.HA solution of 2, 2, 2-trifluoro-1 -(3-nitrophenyl)ethan-1 -one (4.2 g, 19.2 mmol), hydroxylamine hydrochloride (4.0 g, 57.5 mmol) and pyridine (25 mL) in ethanol (25 mL) were heated at reflux for 3 h. or until completion. The solvent was removed in vacuo and the crude product was purified by column chromatography on silica gel using 40% EtOAc-hexanes eluent to give 2, 2, 2- trifluoro-1 -(3-nitrophenyl)ethan-1 -one oxime as a colourless liquid (4.0 g, 89%).19F NMR (233.33 MHz, CDCI3): -66.42 and 62.28 (E and Z oxime).

Molecular Weight:219.12
XLogP3:2.5
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:1
Exact Mass:219.01432748
Monoisotopic Mass:219.01432748
Topological Polar Surface Area:62.9
Heavy Atom Count:15
Complexity:271
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes