Some common heterocyclic compound, 1003-98-1, name is 2-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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. SDS of cas: 1003-98-1
Step 1: Production of 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine To a solution of 2-bromo-4-fluoroaniline (5.0 g, 26.3 mmol) in 1,4-dioxane (50 ml) were added triethylamine (18.5 ml, 132.7 mmol) and [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (PdCl2(dppf)CH2Cl2) (1.07 g, 1.3 mmol) at room temperature. To the mixture was added dropwise pinacolborane (11.5 ml, 79.2 mmol) at room temperature and the mixture was stirred at 100C for 27 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (toluene) to give 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylamine (2.0 g, yield 32.0%). 1H-NMR(400MHz, CDCl3):delta(ppm) 7.28 (1H, d, J=3.2Hz), 6.91 (1H, ddd, J=8.8, 8.8, 3.2Hz), 6.53(1H, dd, J=8.8, 3.6Hz), 4.45(2H, brs), 1.34 (12H, s). MS 238 (M+1).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1003-98-1, its application will become more common.
Reference:
Patent; Japan Tobacco, Inc.; EP1719773; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary