4-Nitrophenol → 1-(2-Methoxyethoxy)-4-nitrobenzene

HRID 1812097노트

반응식

HRID 1812097 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:13][O:14][CH2:15][CH2:16]Br>CN(C=O)C>[CH3:13][O:14][CH2:15][CH2:16][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 9804-NitrophenolHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl ether

생성물 1

HCID 5478091-(2-Methoxyethoxy)-4-nitrobenzene수율 105%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A stirred solution of 4-nitrophenol (Fluka) (0.511 g, 3.67 mmol) in DMF (10 mL) was treated with 60% sodium hydride (Aldrich) (0.170 g, 4.25 mmol) added in portions at 0° C. The yellow mixture was stirred at that temperature for 10 min, then 2-bromoethyl methyl ether (Aldrich) (0.380 mL, 4.04 mmol) was added dropwise at 0° C. The mixture was stirred at that temperature for 5 min, warmed up to rt and stirred for 3.5 h then at 70° C. overnight. The reaction mixture was poured into ice-water (100 mL). The aqueous phase was extracted with EtOAc (2×70 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo to give 1-(2-methoxyethoxy)-4-nitrobenzene (0.753 g, 105% yield) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 8.16-8.25 (m, 2H); 6.95-7.03 (m, 2H); 4.17-4.26 (m, 2H); 3.73-3.84 (m, 2H); 3.46 (s, 3H). m/z (ESI, +ve ion) 198.1 (M+H)+.

후처리

  1. additionadded in portions at 0° C
  2. stirringThe mixture was stirred at that temperature for 5 min
  3. stirringstirred for 3.5 h
  4. customat 70° C.
  5. customovernight
  6. extractionThe aqueous phase was extracted with EtOAc (2×70 mL)
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-31b377ca795b485ca078b9dc1e58e19a
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362241B2

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