1,2-Dibromoethane → 4-[3-(2-Bromo-ethoxy)-4-nitro-phenyl]-morpholine

HRID 1687993노트

반응식

HRID 1687993 반응식
[Br:1][CH2:2][CH2:3]Br.[N:5]1([C:11]2[CH:12]=[CH:13][C:14]([N+:18]([O-:20])=[O:19])=[C:15]([OH:17])[CH:16]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C(=O)([O-])[O-].[K+].[K+].C1(O)C=CC=CC=1.BrC(Br)C>C(#N)C.C(OCC)(=O)C>[Br:1][CH2:2][CH2:3][O:17][C:15]1[CH:16]=[C:11]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[CH:12]=[CH:13][C:14]=1[N+:18]([O-:20])=[O:19]

참가 물질

7

반응물 4

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 27993995-Morpholino-2-nitrophenolHCID 67263526Phenol dibromoethane

생성물 1

HCID 672636974-[3-(2-Bromo-ethoxy)-4-nitro-phenyl]-morpholine수율 38.2%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

1,2-Dibromoethane (1.50 mL, 17.4 mmol) was added to 5-Morpholin-4-yl-2-nitro-phenol (0.792 g, 3.53 mmol) and Potassium carbonate (1.71 g, 12.4 mmol) in Acetonitrile (40 mL) and the reaction was stirred under an atmosphere of Nitrogen at room temperature for 72 h (no change by HPLC), then was brought to reflux. After 4d, 1H-NMR indicated that the assumed starting material my LCMS was in actuality the 2:1 phenol-dibromoethane adduct. The reaction was cooled, diluted with ethyl acetate and filtered, conc. onto 5 g Celite. Chromatography (ISCO, 40 g, 0-40% EtOAc:Hex) afforded 4-[3-(2-Bromo-ethoxy)-4-nitro-phenyl]-morpholine (447 mg, 38%) as a colorless oil. 1H-NMR (CDCl3): 7.99 (d, 1H, J=8.8 Hz), 6.48 (m, 1H), 6.36 (d, 1H, J=1.5 Hz), 4.39 (t, 2H, J=6.8 Hz), 3.85 (t, 4H, J=4.8 Hz), 3.71 (t, 2H, J=6.8 Hz), 3.34 (t, 4H, J=4.8 Hz).

후처리

  1. temperatureto reflux
  2. temperatureThe reaction was cooled
  3. filtrationfiltered, conc. onto 5 g Celite

출처 및 근거

ORD 기록
ord-9ccc6dd9a67e43a2ba29558d90ac6447
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148391B2

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