Dimethyl malonate → 1,3-Dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate

Temperature

100 °C

Dimethyl malonate (13 mL) was added dropwise to 2.7 g sodium hydride suspended in 20 mL dimethylsulfoxide. The mixture was heated to 100° C. for 10 minutes and then cooled to room temperature. 5-Bromo-2-fluoronitrobenzene (5.0 g) in 25 mL of dimethylsulfoxide was added and the mixture was heated at 100° C. for 2 hours. The reaction mixture was cooled and quenched with 300 mL of saturated ammonium chloride solution and extracted three times with ethyl acetate. The extracts were combined, washed with saturated ammonium chloride, water and brine, dried over anhydrous sodium sulfate and concentrated to give crude dimethyl 4-bromo-2-nitrophenylmalonate as a pale yellow oil.

1. temperaturecooled to room temperature
2. temperaturethe mixture was heated at 100° C. for 2 hours
3. temperatureThe reaction mixture was cooled
4. customquenched with 300 mL of saturated ammonium chloride solution
5. extractionextracted three times with ethyl acetate
6. washwashed with saturated ammonium chloride, water and brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated

ORD record

ord-a862e5eca2724f5c963f3310454d1472

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06696463B2