Hydrochloric Acid → (6-Bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester

HRID 1054911Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([OH:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][C:20](=[O:23])[CH2:21]Br.Cl>CS(C)=O>[CH3:18][O:19][C:20](=[O:23])[CH2:21][O:11][C:5]1[C:6]([N+:8]([O-:10])=[O:9])=[N:7][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

6-Bromo-2-nitropyridin-3-ol (10.8 g, 49.1 mmol) was dissolved in dimethylsulfoxide (DMSO) (30 mL). Potassium carbonate (13.6 g, 98.6 mmol) and bromoacetic acid methyl ester (7.0 mL, 74 mmol) were added and the reaction mixture was stirred at 60° C. for two hours. Then, the reaction mixture was cooled to room temperature and neutralized with 1N HCl(aq). The aqueous solution was extracted twice with ethyl acetate, and the combined organic extracts were washed with brine. The product was purified by column chromatography (SiO2, EtOAc/hexanes) to afford (6-bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester. Yield 10.9 g (37.5 mmol, 76%). LCMS (ESI): calc. C8H7BrN2O5=290, 292; obs. Low ionization.

Workup

extractionThe aqueous solution was extracted twice with ethyl acetate
washthe combined organic extracts were washed with brine
customThe product was purified by column chromatography (SiO2, EtOAc/hexanes)

Sources & evidence

ORD record: ord-c7694631f8a24b94987eda083d4570fd
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394315B2

Reaction notes

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