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

HRID 490213

반응식

HRID 490213 반응식
[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]

참가 물질

5

반응물 3

HCID 63582-BromopropaneHCID 69472-NitrophenolHCID 11430Potassium Carbonate

생성물 1

HCID 1971801-(1-Methylethoxy)-2-nitrobenzene수율 88.3%

시약·촉매·용매 1

HCID 18184436N,N-dimethylformamide acetone용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-6fc1a4ae2cd342f1a95baecd8ed7f3f1
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528134B2

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