Synthetic Route of 367-22-6, These common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, 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.
A. 4-Chloro-3-fluorobenzenesulfonyl chloride The title compound was prepared using the method of Organic Syntheses Vol. 60, 121-124. A solution of 4-chloro-3-fluoro aniline (5 g, 0.034 mol) in glacial HOAc (10 mL) was added slowly to concentrated HCl (30 mL) to form a white precipitate. The mixture was cooled in a dry ice-ethanol bath. A solution of NaNO2 (3.08 g, 0.045 mol) in H2O (5 mL) was added dropwise while stirring with a glass rod, maintaining the temperature at or below -5 C. The mixture was stirred intermittently while in the bath for 1 h. In a separate flask, HOAc (40 mL) was saturated with SO2 using a gas dispersion tube (about 15 min). To this acetic acid solution was added cuprous chloride (0.68 g, 7 mmol), which gave a grey solution. The SO2 was bubbled through until the solution turned green-blue. The solution was cooled in a dry ice-ethanol bath and the diazonium salt mixture was added in portions while stirring with a glass rod. After the addition was complete, the reaction was removed from the bath and allowed to come to 0 C. over 15 to 20 min. with occasional stirring. The reaction was poured onto ice (100 mL) and extracted with CH2Cl2 (2*100 mL). The combined organic layer was washed with saturated NaHCO3 (3*40 mL), dried (Na2SO4), filtered and concentrated to afford a golden oil. The crude product was purified by silica gel column chromatography, eluding with a gradient of 10% to 15% CH2Cl2/hexanes to afford the title compound (5.5 g, 70%) as a golden oil. Mass Spectrum (-ESI): 209 [M-Cl+O]-.
Statistics shows that 4-Chloro-3-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 367-22-6.
Reference:
Patent; Wyeth; US2007/249722; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics