Phenol → 1-(2-Methoxy-ethoxy)-3-methyl-2-nitrobenzene

HRID 401611

반응식

HRID 401611 반응식
[CH3:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C1(O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH3:25][O:26][CH2:27][CH2:28]Br>CN(C=O)C.O>[CH3:25][O:26][CH2:27][CH2:28][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[N+:9]([O-:11])=[O:10]

참가 물질

7

반응물 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 210263-Methyl-2-nitrophenolHCID 809722-Bromoethyl methyl ether

생성물 1

HCID 128554961-(2-Methoxy-ethoxy)-3-methyl-2-nitrobenzene

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

The required 1-(2-methoxy-ethoxy)-3-methyl-2-nitrobenzene was prepared from 3-methyl-2-nitrophenol. To a stirred solution of the phenol (2.0 g, 13.1 mmol) in DMF (65 mL) was added potassium carbonate (2.16 g, 15.7 mmol) and bromoethyl methyl ether (1.47 mL, 15.7 mmol) at room temperature. After the mixture was stirred at 50° C. for 48 h, water was added. The mixture was extracted with EtOAc (3×), washed with brine, dried over anhydrous MgSO4 filtered and evaporated. After chromatographic purification on silica gel, 1-(2-methoxy-ethoxy)-3-methyl-2-nitrobenzene was obtained in 85% yield (2.34 g). 1H NMR (500 MHz, CDCl3) δ 7.28 (1H, t, J=8.0 Hz), 6.89 (1H, d, J=9.0 Hz), 6.85 (1H, d, J=8.0 Hz), 4.19 (2H, t, J=4.5 Hz), 3.72 (2H, t, J=5.0 Hz), 3.41 (3H, s), 2.30 (3H, s).

후처리

  1. extractionThe mixture was extracted with EtOAc (3×)
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customAfter chromatographic purification on silica gel

출처 및 근거

ORD 기록
ord-5b8c2a2be6f74fb8b7a7f609036c07b5
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741942B2

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