Phosphoric Acid → HCID 66785177, compound

Temperature

80 °C

2-Bromo-5-fluoro-aniline (5.00 g, 95 mass % article, 25.0 mmol), m-nitrobenzenesulfonic acid (2.65 g, 13.1 mmol), 20.0 mL of 85 wt % aqueous phosphoric acid solution and ferrous sulfate heptahydrate (69.5 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° C. in an oil bath. Subsequently, 2-butylacrolein (7.44 g, 98 mass % 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° C. 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→1/1) using silica gel, followed by drying under reduced pressure to give 1.35 g of 8-bromo-3-butyl-5-fluoroquinoline as a brown solid (yield: 19.2%).

1. customequipped with a magnetic stirrer, a reflux condenser
2. additionAfter completion of the dropwise addition
3. temperaturethe mixture was heated
4. extractionThe neutralized liquid was extracted with dichloromethane
5. customdichloromethane was removed under reduced pressure
6. customThe resulting crude reaction product
7. customwas purified by column chromatography (Hexane/AcOEt=100/0→1/1)
8. customby drying under reduced pressure

ORD record

ord-22025ea07d7546dcaf88c363203a6799

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08137821B2