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

HRID 1041651ノート

反応式

HRID 1041651 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-101c9f3936644fd5b1491b78a4048b73
出典データセット
uspto-grants-2013_10
特許番号
US08552186B2

反応ノート

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