Dimethylformamide → 2-Chloro-1-(2-methoxyethoxy)-4-nitrobenzene

HRID 1159928노트

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HRID 1159928 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[CH3:12][O:13][CH2:14][CH2:15][OH:16].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(#N)C.CCOC(C)=O.O>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:16][CH2:15][CH2:14][O:13][CH3:12]

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 80192-Methoxyethanol2회HCID 11430Potassium Carbonate2회HCID 676882-Chloro-1-fluoro-4-nitrobenzene

생성물 1

HCID 595137122-Chloro-1-(2-methoxyethoxy)-4-nitrobenzene수율 94.7%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

2-Chloro-1-fluoro-4-nitrobenzene (0.8 g, 4.56 mmol) and 2-(methyloxy)ethanol (0.52 g, 6.84 mmol) were combined and dissolved in Acetonitrile (15 mL). Potassium carbonate (2.4 g, 17 mmol) was then added and the resulting mixture was heated at 50° C. for 16 h. The reaction was not complete so additional potassium carbonate (1.0 g, 7.24 mmol) and 2-(methyloxy)ethanol (0.08 g, 1.05 mmol) were added as well as DMF (3 mL) to aid in solubilizing the reaction which was then heated at 85° C. for 16 h. The reaction was cooled to rt then diluted with EtOAc (250 mL) and water (150 mL). The organic layer was separated, washed with brine (100 mL), dried over Na2SO4, filtered and concentrated in vacuo to yield 1.0 g of the compound. 1H NMR (300 MHz, DMSO-d6): δ 8.31 (d, 1H), 8.21 (m, 1H), 7.38 (d, 1H), 4.35 (m, 2H), 3.72 (m, 2H), 3.32 (s, 3H).

후처리

  1. customthe reaction which
  2. temperaturewas then heated at 85° C. for 16 h
  3. temperatureThe reaction was cooled to rt
  4. customThe organic layer was separated
  5. washwashed with brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-65d289923f344eb5b2a509ee71d7beae
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812022B2

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