Hydrochloric Acid → HCID 10038811, compound

In a flask made of glass equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel and having an inner volume of 100 ml were charged 3.40 g (62.9 mmol) of sodium methoxide and 20 ml of dimethyl sulfoxide under argon atmosphere, and then, while stirring at room temperature, 8.31 g (62.3 mmol) of dimethyl malonate with a purity of 99% was gradually added dropwise to the mixture over 5 minutes. After cooling the mixture to 20° C., 5.10 g (31.4 mmol) of 2,4-difluoronitrobenzene was gradually added dropwise to the mixture over 5 minutes, and the temperature of the mixture was raised to 80° C. and the mixture was reacted for one hour. After completion of the reaction, the mixture was cooled to room temperature, and then, 100 ml of ethyl acetate was added to the mixture, and 5.25 ml (31.4 mmol) of 6 mol/l hydrochloric acid was gradually added dropwise to the mixture while stirring. Then, the organic layer was separated, and washed successively with 30 ml of water and 30 ml of a saturated saline solution in this order, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting concentrate was purified by silica gel column chromatography (filler:Daisogel 1002W, eluent:hexane:ethyl acetate=9:1 (volume ratio)) to obtain 6.55 g of dimethyl 2-(5-fluoro-2-nitrophenyl)malonate (isolation yield: 75%) as a white crystal with a purity of 97.2% (areal percentage by high performance liquid chromatography).

1. customIn a flask made of glass
2. customequipped with a stirrer
3. temperatureAfter cooling the mixture to 20° C.
4. temperaturethe temperature of the mixture was raised to 80° C.
5. customthe mixture was reacted for one hour
6. customAfter completion of the reaction
7. temperaturethe mixture was cooled to room temperature
8. additionwas gradually added dropwise to the mixture
9. stirringwhile stirring
10. customThen, the organic layer was separated
11. washwashed successively with 30 ml of water and 30 ml of a saturated saline solution in this order
12. dry with materialdried over anhydrous magnesium sulfate
13. filtrationAfter filtration
14. concentrationthe filtrate was concentrated under reduced pressure
15. concentrationthe resulting concentrate
16. customwas purified by silica gel column chromatography (filler:Daisogel 1002W, eluent:hexane:ethyl acetate=9:1 (volume ratio))

ORD record

ord-da82614a19b14a53aadb0eea8062ae23

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07342040B2