Diethyl methylmalonate → HCID 21708291, compound

2.2 g of 55% sodium hydride was suspended in 30 ml of THF, followed by the addition of 50 ml of a THF solution of 8.65 ml (50.3 mmol) of diethyl methylmalonate under cooling with ice. The obtained mixture was stirred at room temperature for 20 minutes and cooled with ice again, followed by the dropwise addition of 85 ml of a THF solution of the 2-chloro-3-bromo-5-nitrobenzoyl chloride prepared in the above Example. The obtained mixture was stirred as such for 1.5 hours and then poured into an aqueous solution of ammonium chloride. The resulting mixture was extracted with ethyl acetate. The ethyl acetate phase was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated brine, dried and distilled to remove the solvent. 30 ml of methylene chloride was added to the residue. The resulting mixture was freed from insolubles by filtration and concentrated under reduced pressure to give 21.77 g of the title compound (yield: quantitative).

1. temperatureunder cooling with ice
2. temperaturecooled with ice again
3. stirringThe obtained mixture was stirred as such for 1.5 hours
4. extractionThe resulting mixture was extracted with ethyl acetate
5. washThe ethyl acetate phase was washed with a saturated aqueous solution of sodium hydrogen carbonate
6. dry with materiala saturated brine, dried
7. distillationdistilled
8. customto remove the solvent
9. addition30 ml of methylene chloride was added to the residue
10. filtrationThe resulting mixture was freed from insolubles by filtration
11. concentrationconcentrated under reduced pressure

ORD record

ord-01fa66b7342d4c59add607db35b3cb84

Source dataset

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06281214B1