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

HRID 1159928ノート

反応式

HRID 1159928 の反応式
[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]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 80192-Methoxyethanol2 回HCID 11430Potassium Carbonate2 回HCID 676882-Chloro-1-fluoro-4-nitrobenzene

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-65d289923f344eb5b2a509ee71d7beae
出典データセット
uspto-grants-2010_10
特許番号
US07812022B2

反応ノート

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