Hydrochloric Acid → HCID 59718741, compound

Sodium hydride (60% oiliness) (0.33 g, 8.25 mmol) was added in the dimethylformamide (20 mL) solution of diethyl malonate (1.23 mL, 8.14 mmol) while cooling the solution with ice, and the mixture was directly stirred for 4 hours. 5-bromo-2-nitrobenzotrifluoride (2.0 g, 7.41 mmol) was added in the reaction mixture while cooling it with ice, and the temperature was raised to room temperature and then the mixture was further heated and stirred at 70° C. for 3 hours. After the reaction solution was poured into ice water and acidified with 2N hydrochloric acid, the solution was extracted with ethyl acetate. After the organic layer had been washed with 5% sodium hydrogencarbonate aqueous solution and then with water and dried over anhydrous sodium sulfate, the solvents were concentrated under reduced pressure. The residue was subjected to silica gel column chromatograph (45 g) and was eluted with the mixture of ethyl acetate and n-hexane of 1:5 in mixing ratio. The eluted liquid was concentrated under reduced pressure and yellow oily diethyl 2-(4-nitro-3-trifluoromethyl-phenyl)-malonate (1.1 g, 42%) was obtained.

1. temperaturewhile cooling the solution with ice
2. temperaturewhile cooling it with ice
3. temperaturethe mixture was further heated
4. stirringstirred at 70° C. for 3 hours
5. extractionthe solution was extracted with ethyl acetate
6. washAfter the organic layer had been washed with 5% sodium hydrogencarbonate aqueous solution
7. dry with materialwith water and dried over anhydrous sodium sulfate
8. concentrationthe solvents were concentrated under reduced pressure
9. washwas eluted with the mixture of ethyl acetate and n-hexane of 1:5
10. additionin mixing ratio
11. concentrationThe eluted liquid was concentrated under reduced pressure

ORD record

ord-1c7dfad4e68846f6b31750c59ebafe7b

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367666B2