Reference of 32338-02-6,Some common heterocyclic compound, 32338-02-6, name is 2-Bromo-4-methoxyaniline, molecular formula is C7H8BrNO, 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.
Example 4 4-Methoxy-2-((trimethylsilyl)ethynyl)aniline (Compound 7) Compound 6 (1.40 g, 6.97 mmol), triphenylphosphine (55 mg, 3 mol percent) and copper (I) iodide (13 mg, 1 mol percent) were added to an oven-dried reaction flask containing toluene (27 mL) and Et3N (7 mL). The reaction mixture was stirred at room temperature for 5 min with N2 (g) bubbling. Bis(triphenylphosphine)palladium (II) dichloride (48 mg, 1 mol percent) and a solution of trimethylsilylacetylene (1.49 mL, 10.46 mmol) in Et3N (3 mL) were added. The reaction mixture was stirred at 100¡ã C. for 24 h. The reaction was cooled to room temperature, then diluted with EtOAc (300 mL) and washed with brine (3*70 mL). The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (8percent EtOAc in hexanes) to afford compound 7 in 70.0percent (1.07 g) yield as a brown oil. 1H-NMR (CDCl3, 400 MHz) delta 6.81 (1H, s, Ar), 6.74 (1H, d, J=8.8 Hz, Ar), 6.63 (1H, d, J=8.8 Hz, Ar), 3.70 (3H, s, OCH3), 3.50 (2H, bs, NH2), 0.24 (9H, s, Si(CH3)3); 13C-NMR (CDCl3, 100 MHz) delta 151.7, 142.4, 117.7, 115.8, 115.6, 108.3, 101.7, 99.7, 55.7, 0.08; MS (ESI) m/z Calcd for C12H17NOSi (M+): 219.1, Found: 220.1 (M+H+).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-methoxyaniline, its application will become more common.
Reference:
Patent; UNIVERSITY OF MARYLAND, BALTIMORE; FLETCHER, Steven; US2014/256817; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem