2-Bromopropane → 1-(1-Methylethoxy)-2-nitrobenzene

HRID 490213

Reaktionsgleichung

Reaktionsgleichung von HRID 490213
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH:17](Br)([CH3:19])[CH3:18]>CN(C)C=O.CC(C)=O>[CH:17]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])([CH3:19])[CH3:18]

Komponenten

5

Edukt 3

HCID 63582-BromopropaneHCID 69472-NitrophenolHCID 11430Potassium Carbonate

Produkt 1

HCID 1971801-(1-Methylethoxy)-2-nitrobenzeneAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18184436N,N-dimethylformamide acetoneLösungsmittel

Versuchsvorschrift

A solution of 2-nitrophenol (10 g, 71.9 mmol) and potassium carbonate (21.85 g, 158.1 mmol) in N,N-dimethylformamide:acetone (1:2, 150 mL) was heated under reflux and isopropyl bromide (14.8 mL, 158 mmol) was added dropwise (in 30 minutes) during reflux and stirred overnight. The reaction was cooled to room temperature and partitioned between water and ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (10% ethyl acetate:hexanes) to provide the title compound as a golden yellow oil (11.5 g, 88%). 1H NMR (300 MHz, CDCl3) δ 1.4 (d, 6H, J=6 Hz), 4.7 (septet, 1H, J=6 Hz), 6.98 (m, 1H), 7.09 (d, 1H, J=9 Hz), 7.45 (m, 1H), 7.78 (dd, 1H, 3 Hz); MS (DCI/NH3) m/e 182 (M+H)+.

Aufarbeitung

  1. temperatureunder reflux
  2. temperatureduring reflux
  3. custompartitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel (10% ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6fc1a4ae2cd342f1a95baecd8ed7f3f1
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528134B2

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