4-Nitro-2-trifluoromethylphenol

A solution of 6-methoxy-5-nitrobenzotrifluoride (24.73 g, 110.7 mmol) in acetic acid (260 ml) and aqueous HBr solution (62percent, 130 ml) was heated to reflux for 96 h, cooled, evaporated and taken up in aqueous saturated NaHCO3 solution/Et2O (3x). The organic phases were washed with aqueous 10percent NaCl, dried over Na2SO4 and evaporated to yield 19.27 g (83percent) of 4-nitro-2-trifluoromethyl-phenol as yellow solid, MS: 207 (M+), MP: 103-104 C.A mixture of l-methoxy-4-nitro-2- (trifluoromethyl) benzene (10.29 g, 46.5 mmol) , lithium chloride (5.92 g, 140 mmol) and N, N-dimethylformamide (46.5 mL) was heated under reflux for 6.5 hr. After cooling to room temperature, 10percent aqueous sodium hydroxide solution (230 mL) was added, and the mixture was washed with ethylether (χ2) . The aqueous solution was acidified with 10percent hydrochloric acid, and extracted with ether (χ2) . The- extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=80/20) to give the title compound (6.20 g, 65percent) .Lithium chloride (2.30 g) was added to a solution of 1-methoxy-4-nitro-2-(trifluoromethyl)benzene (4 g) in N, N-dimethylformamide (40 ml) at room temperature. The reaction mixture was stirred at 160 °C for 5 h. After cooling to rt, the solution was diluted with EtOAc (300 ml). The mixture was washed with water (100 ml * 2) and brine (100 ml), dried and concentrated to give 4-nitro-2-(trifluoromethyl)phenol (3.5 g) as a yellow solid.1-Chloro-4-nitro-2-(trifluoromethyl)benzene (2.0 mL, 13.3 mmole) was dissolved in dimethyl sulfoxide (DMSO, 12 mL), NaOH (1.6 g) was batchwise added at a temperature lower than 25° C., and the reaction solution was reacted at room temperature (RT) for 8 hours. After the reaction was terminated, the pH of the reaction solution was adjusted to 1.0 using concentrated HCl, and then the reaction solution was poured into the separatory funnel and extracted with CHGeneral procedure: A solution of 0.50 g (1.51 mmol) of 1a and an excess amount of base a in the appropriate base (10 mL) was stirred for 7 h at room temperature. The solvent was removed invacuo and the residue was extracted with CH

Molecular Weight:207.11
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Exact Mass:207.01432748
Monoisotopic Mass:207.01432748
Topological Polar Surface Area:66
Heavy Atom Count:14
Complexity:225
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes