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

HRID 1054911ノート

反応式

HRID 1054911 の反応式
[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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 218738086-Bromo-2-nitropyridin-3-ol

生成物 1

HCID 90011186(6-Bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-c7694631f8a24b94987eda083d4570fd
出典データセット
uspto-grants-2016_07
特許番号
US09394315B2

反応ノート

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