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

HRID 1054911노트

반응식

HRID 1054911 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c7694631f8a24b94987eda083d4570fd
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394315B2

반응 노트

불러오는 중…