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

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-Eintrag

ord-03d6d163236f49ce8eace9b37837f7b1

Quelldatensatz

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06313158B1