Dimethylformamide → Dimethyl 2-(5-bromo-3-nitropyridin-2-YL)malonate

HRID 1618505Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:18]([O:25][CH3:26])(=[O:24])[CH2:19][C:20]([O:22][CH3:23])=[O:21].CN(C=O)C>>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([CH:19]([C:18]([O:25][CH3:26])=[O:24])[C:20]([O:22][CH3:23])=[O:21])=[N:6][CH:7]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 7943Dimethyl malonate

HCID 11430Potassium Carbonate

HCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 53217420Dimethyl 2-(5-bromo-3-nitropyridin-2-YL)malonate

Procedure

Prepared according to procedure G using 5-bromo-2-chloro-3-nitropyridine (25 g, 105 mmol) and potassium carbonate (44 g, 316 mmol), dimethyl malonate (18 mL, 158 mmol) in DMF (105 mL, 105 mmol). After purification dimethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate was obtained as a dark liquid. Mass Spectrum (ESI) m/e=333 [(M+1) (79Br)] and 335 [(M+1) (81Br)].

Workup

customPrepared
customAfter purification dimethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate
customwas obtained as a dark liquid

Sources & evidence

ORD record: ord-f33eb5674523432091dd39ee36f53bec
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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