A kind of method of synthesizing 2-fluoroaniline compound
A compound, the technology of fluoroaniline, which is applied in the field of synthesizing 2-fluoroaniline compounds, can solve the problems that the ortho fluorination reaction of aniline derivatives has not been realized, and achieve high practical value, wide substrate adaptability, and fluorination selection good sex effect
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Embodiment 1
[0057]
[0058] [1] Aniline (0.93 g, 10.0 mmol), bromide (43.0 mg, 0.3 mmol), pyridine (71.2 mg, 0.9 mmol), and 40 ml of toluene were added to 100 ml of flask. The mixture was heated to 60 ° C in an air environment for 20 hours and then the TLC detection reaction was completed. The reaction liquid is cooled to room temperature, distilled the solvent under reduced pressure, and the residue is separated from the column chromatography [GF254 silica gel; 100-200 mesh; the opening agent is petroleum ether], collects purification, collect the eluent containing the product, eluent distilled solvent The azobenzene was obtained (96% yield).
[0059] [2] Azobenzene (91.1 mg, 0.5 mmol), bis (dibenzyl acetone) palladium (28.8 mg, 0.05 mmol), N-fluorozophenylsulfonamide (0.315 g) was added to a closed reaction vessel. 1 mmol), potassium nitrate (20.2 mg, 0.2 mmol), ethyl acetate (2.5 mL). The reaction mixture was stirred at 55 ° C for 12 h. The reaction was stopped, and the mixture was dilut...
Embodiment 2
[0063]
[0064] [1] Aniline (0.93 g, 10.0 mmol), bromide (43.0 mg, 0.3 mmol), pyridine (71.2 mg, 0.9 mmol), and 40 ml of toluene were added to 100 ml of flask. The mixture was heated to 60 ° C in an air environment for 20 hours and then the TLC detection reaction was completed. The reaction liquid is cooled to room temperature, distilled the solvent under reduced pressure, and the residue is separated from the column chromatography [GF254 silica gel; 100-200 mesh; the opening agent is petroleum ether], collects purification, collect the eluent containing the product, eluent distilled solvent The azobenzene was obtained (96% yield).
[0065] [2] Azobenzene (91.1 mg, 0.5 mmol), bis (dibenzyl acetone) palladium (14.4 mg, 0.025 mmol), N-fluoroisolabisulfonamide (0.315 g) is added to a closed reaction vessel. 1 mmol), potassium nitrate (20.2 mg, 0.2 mmol), ethyl acetate (2.5 mL). The reaction mixture was stirred at 55 ° C for 12 h. The reaction was stopped, and the mixture was dilute...
Embodiment 3
[0069]
[0070] [1] Aniline (0.93 g, 10.0 mmol), bromide (43.0 mg, 0.3 mmol), pyridine (71.2 mg, 0.9 mmol), and 40 ml of toluene were added to 100 ml of flask. The mixture was heated to 60 ° C in an air environment for 20 hours and then the TLC detection reaction was completed. The reaction liquid is cooled to room temperature, distilled the solvent under reduced pressure, and the residue is separated from the column chromatography [GF254 silica gel; 100-200 mesh; the opening agent is petroleum ether], collects purification, collect the eluent containing the product, eluent distilled solvent The azobenzene was obtained (96% yield).
[0071] [2] Azobenzene (91.1 mg, 0.5 mmol), bis (dibenzyl acetone) palladium (14.4 mg, 0.025 mmol), N-fluoro-bisphenylsulfonamide (0.157 g) is added to a closed reaction vessel. 0.5 mmol), potassium nitrate (20.2 mg, 0.2 mmol), ethyl acetate (2.5 mL). The reaction mixture was stirred at 55 ° C for 12 h. The reaction was stopped, and the mixture was d...
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