2,4,6-Trifluorobenzonitrile

white to light yellow crystal powder

a) To a solution of 2, 4, 6-trifluurobenzonitrile (1) (5g, 31.8 mmol, 1 eq.) in 50 mL of ethanol heated to 60C, was added hydrazine hydrate (50-60% solution) (3.4g, 63.6 mmol, ~2 eq.). ETpon consumption of 1 (monitored using TLC), the solvent was evaporated from the reaction mixture under vacuum. To the remaining white semisolid mass was added 50 mL water and the organic mass was extracted with ethyl acetate (3 X 50mL). The combined organic fractions were combined and washed with brine (100 mL). The organic fraction was separated and dried over sodium sulfate. Subsequently, evaporation of the organic layer provided ~6.5 g of white mixture that was utilized in the next reaction without further purification The above obtained crude product (6g, 35.5 mmol, 1 eq.) was suspended in lOOmL ethanol in a 250mL capacity sealed reaction vessel. 2-acetyldimedone (16. lg, 88.75 mmol, 2.5 eq), an orange colored oil, was subsequently added to the reaction vessel which was sealed and heated to l00C for 6 hr. The reaction vessel was allowed to cool to rt, ethanol was removed in vacuo, and the remaining mass was extracted with ethyl acetate (3X 100 mL) and water (200 mL). Organic layers were combined and washed with 100 mL water. Separated organic layer was dried using sodium sulfate and adsorbed onto silica, and purified using columnchromatography (S1O2, 3 :2 hexanes/ethyl acetate) to afford 2, 6-difluoro-4-(3, 6, 6-trimethyl-4- oxo-4, 5, 6, 7-tetrahydro-lH-indazol-l-yl)benzonitrile (2) (5.8 g, 52%) as light-yellow solid. 1H NMR (500 MHz, Chloroform-d) d 7.39 - 7.33 (m, 2H), 2.91 (s, 2H), 2.55 (s, 3H), 2.45 (s, 2H), 1.17 (s, 6H). 13C NMR (126 MHz, Chloroform-d) d 192.9, 164.5 (d, J = 6.5 Hz), 162.5 (d, J = 6.4 Hz), 151.8, 149.4, 144.5 - 144.1 (m), 118.8, 108.5, 106.2 (d, J = 4. l Hz), 106.0 (d, J = 3.9 Hz), 99.9, 52.0, 38.0, 36.0, 28.4 (2), 13.3. HRMS (ESI) m/z [M+H] calculated for C17H16F2N3O, 316.1261, found 316.1237.In one embodiment, The 6 mmol of the second reactant was dissolved in 15 ml to 25 ml of the first solvent tetrahydrofuran, and then 0.5 mmol to 2 mmol of the first additive sodium hydride was slowly added.The reaction is carried out for 20-50 minutes under room temperature conditions and under nitrogen.Then 2 second of the first reactant was added to continue the reaction for 12 hours.A mixture comprising the electroluminescent material is obtained.The mixture of the electroluminescent material is cooled to room temperature and poured into distilled water.Extraction with a second extraction solvent, and then washing with a second detergent, Drying with a second desiccant, and then performing chromatography, Obtaining a second crude product, and then eluting with a second eluent to obtain the electroluminescent material, wherein the electroluminescent material is a white solid, The yield was 54%.

Molecular Weight:157.09
XLogP3:1.9
Hydrogen Bond Acceptor Count:4
Exact Mass:157.01393355
Monoisotopic Mass:157.01393355
Topological Polar Surface Area:23.8
Heavy Atom Count:11
Complexity:173
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes