1,3-Dibromopropane → 2-(3-Bromopropoxy)-1-methoxy-4-nitrobenzene

HRID 1057988노트

반응식

HRID 1057988 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].[Br:19][CH2:20][CH2:21][CH2:22]Br>CN(C)C=O.ClCCl>[Br:19][CH2:20][CH2:21][CH2:22][O:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

참가 물질

6

반응물 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 694712-Methoxy-5-nitrophenol

생성물 1

HCID 186726462-(3-Bromopropoxy)-1-methoxy-4-nitrobenzene

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
90 °C

실험 절차

A stirred mixture of 2-methoxy-5-nitrophenol (5.0 g. 29.6 mmol) and powdered potassium carbonate (6.5 g, 47.4 mmol) in dimethylformamide (50 mL) was treated with 1,3-dibromopropane (80.8 g, 0.4 mol), heated to 90° C. for 2 h, cooled, diluted with dichloromethane (250 mL), and filtered. The filtrate was concentrated in vacuo and the residue was crystallized from methanol. The resulting solid was triturated with 30% ethyl acetate/hexane and then with boiling 30% ethyl acetate/hexane. The combined organic phases were concentrated in vacuo to give the title compound: 1H NMR (300 MHz, CDCl3) δ7.92 (dd, 1H), 7.75 (d, 1H), 6.92 (dd, 1H), 4.20 (t, 2H), 3.95 (s, 3H), 3.62 (t, 2H), 2.40 (m, 2H).

후처리

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was crystallized from methanol
  5. customThe resulting solid was triturated with 30% ethyl acetate/hexane
  6. concentrationThe combined organic phases were concentrated in vacuo

출처 및 근거

ORD 기록
ord-0c9b52799a784be0bfb5b459fa1cf985
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06515027B1

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