2,3,5-TRIFLUOROANILINE

General procedure: Polyhalogenarene was placed into a steel autoclave equipped with two inlet/outlet valves. The required amount of anhydrous liquid NH9.3g (0.1 mol) of aniline was added to 50 mL of glacial acetic acid, and 8.2 g (0.12 mol) of sodium nitrite was added at 10 °C. Then slowly dropping dissolved sodium borofluoride 33g (0.3mol) aqueous solution 50mL, maintaining the same temperature, The reaction was filtered after suction for a period of time, then ethyl acetate was added 100mL extraction reaction three times, the combined organic phase, The organic phase was sequentially washed with 10 mL of an aqueous solution of sodium borofluoride and 50 mL of pure water, finally, the organic phase was evaporated to dryness 2, 3, 5-trifluoroaniline 9g.9.3 g (0.1 mol) of aniline was added to 50 mL of glacial acetic acid, Add 8.2 g (0.12 mol) of sodium nitrite at 10° C., and slowly add dropwise 50 mL of an aqueous solution containing 40 g of sodium fluoborate (0.36 mol), and keep the temperature constant. After filtration, add the ethyl acetate 100 mL. The reaction solution was extracted three times, and the organic phases were combined. The organic phase was washed sequentially with 10 mL of an aqueous solution of sodium borofluoride and 50 mL of pure water.Finally, the organic phase is evaporated to give2, 3, 5-Trifluoroaniline 13g.Example 6 : Preparation of 2, 3, 5-trifluoroaniline by a 1 batch-2 stage method A mixture of 9.85 g (0.05 mole) of 4-amino-2, 5, 6-trifluoroisophthalonitrile and 40 g of sulfuric acid in a concentration of 95.5% and containing 1.8 g (0.1 mole) of water was stirred for 30 minutes at 100 to 110C. while keeping the temperature of the reaction mixture at no higher than 100C, 21.8 g (1.21 moles) of water was added dropwise to adjust the concentration of sulfuric acid to 63.7%, and the mixture was stirred for 1 hour while heating under reflux. After cooling it to 50C, the reaction mixture was extracted with 50 ml of toluene. Further, the extraction with 50 ml of toluene was repeated additional three times. The toluene layer was separated and dried over anhydrous sodium sulfate, followed by filtering solids. Evaporation of the toluene under reduced pressure afforded a pale yellow liquid of 2, 3, 5-trifluoroaniline. Amount 6.6 g (yield 90.7%) The pale yellow liquid thus obtained had the following infrared absorption spectrum and NMR spectrum, which coincided with the spectral data of standard 2, 3, 5-trifluoroaniline. IR (cmmin1): 3480, 3370, 1640, 1510, 1220, 1115, 1100, 970, 815, 760; 1H-NMR (CDCl3): 3.96 ppm (br), 6.25 ppm (m); 19F-NMR (DMSO-d6): -115.15 ppm (m, 1F), -134.55 ppm (m, 1F), -165.09 ppm (m, 1F) After decoupling of proton: -115.15 ppm (q, 1F), -134.55 ppm (q, 1F), -165.09 ppm (q, 1F)2, 3, 5-Trifluoroaniline 15g (0.1mol) was added to 100mL of a 10% strength sulfuric acid solution, 10 mL of pyridine was added, and the reaction temperature was maintained at room temperature.Slowly add a solution of 20 g (0.3 mol) sodium nitrite.After the addition, keep the room temperature unchanged.20 mL of a 50% strength hypophosphorous acid solution was added dropwise, and the reaction solution was extracted with chloroform (100 mL) three times. The organic phases were combined and evaporated to give 95 g of 1, 2, 4-trifluorobenzene.Add deionized water, glacial acetic acid and In a 2000 mL reaction flask, 9.3g (0.1 mol) of aniline was added to 50 mL of glacial acetic acid, and 8.2 g (0.12 mol) of sodium nitrite was added at 10 C. Then slowly dropping dissolved sodium borofluoride 33g (0.3mol) aqueous solution 50mL, maintaining the same temperature, The reaction was filtered after suction for a period of time, then ethyl acetate was added 100mL extraction reaction three times, the combined organic phase, The organic phase was sequentially washed with 10 mL of an aqueous solution of sodium borofluoride and 50 mL of pure water, finally, the organic phase was evaporated to dryness 9.3 g (0.1 mol) of aniline was added to 50 mL of glacial acetic acid, Add 8.2 g (0.12 mol) of sodium nitrite at 10 C., and slowly add dropwise 50 mL of an aqueous solution containing 40 g of sodium fluoborate (0.36 mol), and keep the temperature constant. After filtration, add the ethyl acetate 100 mL. The reaction solution was extracted three times, and the organic phases were combined. The organic phase was washed sequentially with 10 mL of an aqueous solution of sodium borofluoride and 50 mL of pure water.Finally, the organic phase is evaporated to give2, 3, 5-Trifluoroaniline 13g.

Molecular Weight:147.10
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:147.02958362
Monoisotopic Mass:147.02958362
Topological Polar Surface Area:26
Heavy Atom Count:10
Complexity:120
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes