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

HRID 490213

反応式

HRID 490213 の反応式
[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]

参加物

5

反応物 3

HCID 63582-BromopropaneHCID 69472-NitrophenolHCID 11430Potassium Carbonate

生成物 1

HCID 1971801-(1-Methylethoxy)-2-nitrobenzene収率 88.3%

試薬・触媒・溶媒 1

HCID 18184436N,N-dimethylformamide acetone溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-6fc1a4ae2cd342f1a95baecd8ed7f3f1
出典データセット
uspto-grants-2009_05
特許番号
US07528134B2

関連ノート

読み込み中…