4-Amino-3,5-difluorobenzonitrile

A mixture suspension of 4-bromo-2, 6-difluoroaniline (7, 25.85 g) and copper(I) cyanide (16.70 g) in NMP (60 mL) was stirred at reflux temperature for 1.5 h and then cooled down to room temperature. To the mixture was added 1, 2-diaminoethane (23 mL) and the mixture was poured into water (150 mL). The mixture was extracted with ethyl acetate and the organic layer was washed with 10 wt percent 1, 2-diaminoethane solution in water and water, and then dried. The desiccant was removed by filtration and the filtrate was evaporated in vacuo. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 8 (16.54 g, 86percent) as a pale yellow solid: A mixture of the solid and CuCN in DMF was heated with reflux for 2 days and then filtered through celite. The filtrate was dissolved in methylene chloride and water, and the aqueous phase was extracted with methylene chloride. The combined organic layer was washed with brine, dried over anhyd. MgSO7 (2.03 g, 13.17 mmol) was dissolved in 20 mL of EtOAc and cooled to -10 C with a salt/ice bath. NOBF4(1.54 g, 13.17 mmol) was added in small portions and the reaction mixture was stirred at this temperatureunder Ar. After 1 h, the resulting suspension was filtered over a glass filter and the collected solid waswashed with Et2O (2 × 40 mL) and dried under vacuum to afford 8 (1.8 g, 54%) as a white powder

Molecular Weight:154.12
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:154.03425446
Monoisotopic Mass:154.03425446
Topological Polar Surface Area:49.8
Heavy Atom Count:11
Complexity:174
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes