Electric Literature of 6358-77-6,Some common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-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.
General procedure: A mixture of sydnone (1 eq.), aryl halide (1.5 eq.), palladium acetate (5mol %), XPhos (10mol%) and potassium carbonate (2 eq.) in DMF (0.5 M) under an atmosphere of nitrogen was heated at 80 C (for 3-alkylsydnones) or 120 C (for 3-arylsydnones) for 14 h before the reaction was allowed to cool to r.t. and water was added. The resulting mixture was extracted with ethyl acetate:40-60 petroleum ether (9:1) and the combined organic layers dried over MgSO4 and concentrated in vacuo. Flash silica chromatography (eluting solvent 20%-100% ethyl acetate in 40-60 petroleum ether) afforded the target 3,4-diarylsydnones. The compounds could be further purified by recrystallisation from ethanol or dichloromethane/petrol.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-methoxyaniline, its application will become more common.
Reference:
Article; Brown; Harrity; Tetrahedron; vol. 73; 22; (2017); p. 3160 – 3172;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem