These common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 77326-36-4
Example 24d 2-amino-6-(2-amino-2-methylpropoxy)benzonitrile To a solution of 2-amino-2-methylpropan-1-ol (14.4 g, 161 mmol) in anhydrous THF (150 mL) was added NaH (6.8 g, 161 mmol, 60% in mineral oil) in small portions at 0 C. under nitrogen. The mixture was stirred at 0 C. for 30 minutes and then stirred at room temperature for another 30 minutes. The solution was cooled down to 0 C. again, and to this solution was added dropwise a solution of 2-amino-6-fluorobenzonitrile (20.0 g, 147 mmol) in anhydrous THF (50 mL). The reaction mixture was then refluxed overnight under nitrogen. The reaction mixture was cooled down to room temperature and carefully quenched with aqueous NH4Cl solution and extracted with ethyl acetate (3*). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude mixture was purified by chromatography on silica gel eluting with 10% MeOH in DCM to give the title compound as yellow solid (23.4 g 71%). 1H NMR (400 MHz, DMSO-d6) delta 1.08 (s, 6H), 3.15 (s, 2H), 3.64 (s, 2H), 5.98 (s, 2H), 6.13 (d, J=8.0 Hz, 1H), 6.31 (d, J=8.4 Hz, 1H), 7.15 (t, J=8.4 Hz, 1H). MS 236 (MH+).
The synthetic route of 2-Amino-6-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SENOMYS, INC.; US2011/245353; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts