Application of 1003-99-2, A common heterocyclic compound, 1003-99-2, name is 2-Bromo-5-fluoroaniline, molecular formula is C6H5BrFN, 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.
2-Bromo-5-fluoro-aniline (5.00 g, 95 mass percent article, 25.0 mmol), m-nitrobenzenesulfonic acid (2.65 g, 13.0 mmol), 20.0 mL of 85 wtpercent aqueous phosphoric acid solution and ferrous sulfate heptahydrate (65.5 mg, 0.250 mmol) were placed in a 100 mL three-neck flask equipped with a magnetic stirrer, a reflux condenser, a thermometer and a dropping funnel and the mixture was heated to 80¡ãC in an oil bath. Subsequently, trans-2-hexenal (6.51 g, 98 mass percent article, 65.0 mmol) was added dropwise thereto through the dropping funnel for 1 hour. After completion of the dropwise addition, the mixture was heated and stirred at 100¡ãC for 2 hours. Then, the reaction mixture was poured into water and neutralized to pH 7 by ammonia water. The neutralized liquid was extracted with dichloromethane, and then dichloromethane was removed under reduced pressure. The resulting crude reaction product was purified by column chromatography (Hexane/AcOEt=100/0->1/10) using silica gel, followed by drying under reduced pressure to give 625 mg of 8-bromo-5-fluoro-2-propylquinoline as a yellowish white solid (yield: 9.33percent). 1H-NMR (300 MHz, CDCl3) delta: 8.32 (d, 1H), 7.95-7.90 (m, 1H), 7.40 (d, 1H), 7.08-7.01 (m, 1H), 3.05-3.00 (m, 2H), 1.95-1.85 (m, 2H), 1.05 (t, 3H) [MS] EI (m/z): 268 (M+), CI (m/z): 269 (MH+)
The synthetic route of 1003-99-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Ube Industries, Ltd.; EP1847545; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary