Hydrochloric Acid → HCID 58232217, compound

HRID 2061103Notes

Reaction equation

[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:15]=1[F:23].Cl>C1COCC1>[CH2:8]([O:7][C:1](=[O:6])[CH:2]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:15]=1[F:23])[C:3](=[O:4])[CH3:5])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl acetoacetate (37.4 mL, 294 mmol) was added at 0° C. to a suspension of sodium hydride (65%, 10.8 g) in THF (600 mL), and the mixture was stirred at 0° C. for 30 minutes. It was added dropwise at 0° C. to a solution of 1-bromomethyl-2-fluoro-3-nitrobenzene (compound 1a-1) (68.7 g, 294 mmol) in THF (400 mL), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was then poured into 0.5N hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate. A crude product was obtained by vacuum concentration, and purified by column chromatography (ethyl acetate:hexane=1:3) to yield the title compound (52.2 g, 63%) as a yellow oil.

Workup

stirringthe reaction mixture was stirred at room temperature overnight
extractionextracted with ethyl acetate
extractionThe organic extract
washwas washed with saturated saline
dry with materialdried over magnesium sulfate
customA crude product was obtained by vacuum concentration
custompurified by column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record: ord-3b1801ad7d964ff5b6bab7596d8569e0
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278465B2

Reaction notes

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