2-Amino-5-Bromo-3-Nitrobenzotrifluoride

Step B4-bromo-2-nitro-6-(trifluoromethyl)aniline[00234] Sulfuric acid (350 ml) was cooled to 5 °C in an ice-bath before V-[4-bromo-2- (trifluoromethyl)phenyl]acetamide (100 g, 355 mmol) was added portion-wise. The observed internal temperature increased from 5 °C to 10 °C. After the solids dissolved and temperature decreased to 5 °C, nitric acid (70percent) (43.8 ml) was added slowly drop-wise at such a rate that the internal temperature did not increase above 10 °C. The temperature was carefully controlled between 8 °C and 12 °C until the reaction was complete. The cold dark solution was carefully poured into stirring ice water (2L, mostly ice). The tan precipitate was collected by filtration and the filter cake washed with 1 L of cold water before being air dried. The tan powder was slurried in methanol (500 mL) in a 3L 3-neck flask, and concentrated hydrochloric acid (37percent) (750 mL, 9130 mmol) was added and the mixture heated with a heating mantel to 100 °C. Excessive frothing occurred. 10OmL of 1 , 4-dioxane and 200mL of tetrahydrofuran were added to help the frothing subside. Frothing did not subside. The reaction temperature was brought down to 80 °C and heated overnight. The mixture was much more manageable and frothing was better controlled. The mixture was slowly heated to 95 °C and was stirred for 72 hours. The mixture was cooled to room temperature and extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated to give the title compound (101 g, 99percent). Step H 4-bromo-2-nitro-6-(trifluoromethyl)aniline[00315] A solution of /V-(4-bromo-2-nitro-6-(trifluoromethyl)phenyl)acetamide (7.30 g, 22.5 mmol) in cone. HCI (100 mL) was heated at 110 °C overnight. The reaction mixture was basified with sat. NaHC0C. 4-Bromo-2-nitro-6-trifluoromethyl-phenylamine2-Nitro-6-trifluoromethyl-phenylamine (10.0 g, 48.5 mmol) was placed in a 200 mL round-bottom flask equipped with a magnetic stir bar. Glacial acetic acid (100 mL) and bromine (3.24 mL, 63.1 mmol) were added, and the mixture was stirred at RT for 18 h. The mixture was poured into ice (200 mL), and the excess bromine was quenched with 10 percent aq Na

Molecular Weight:285.02
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Exact Mass:283.94082
Monoisotopic Mass:283.94082
Topological Polar Surface Area:71.8
Heavy Atom Count:15
Complexity:256
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes