1,3-Dibromopropane → 2-(3-Bromopropoxy)-1-methoxy-4-nitrobenzene

HRID 1057988ノート

反応式

HRID 1057988 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].[Br:19][CH2:20][CH2:21][CH2:22]Br>CN(C)C=O.ClCCl>[Br:19][CH2:20][CH2:21][CH2:22][O:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

参加物

6

反応物 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 694712-Methoxy-5-nitrophenol

生成物 1

HCID 186726462-(3-Bromopropoxy)-1-methoxy-4-nitrobenzene

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
90 °C

実験手順

A stirred mixture of 2-methoxy-5-nitrophenol (5.0 g. 29.6 mmol) and powdered potassium carbonate (6.5 g, 47.4 mmol) in dimethylformamide (50 mL) was treated with 1,3-dibromopropane (80.8 g, 0.4 mol), heated to 90° C. for 2 h, cooled, diluted with dichloromethane (250 mL), and filtered. The filtrate was concentrated in vacuo and the residue was crystallized from methanol. The resulting solid was triturated with 30% ethyl acetate/hexane and then with boiling 30% ethyl acetate/hexane. The combined organic phases were concentrated in vacuo to give the title compound: 1H NMR (300 MHz, CDCl3) δ7.92 (dd, 1H), 7.75 (d, 1H), 6.92 (dd, 1H), 4.20 (t, 2H), 3.95 (s, 3H), 3.62 (t, 2H), 2.40 (m, 2H).

後処理

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was crystallized from methanol
  5. customThe resulting solid was triturated with 30% ethyl acetate/hexane
  6. concentrationThe combined organic phases were concentrated in vacuo

出典と根拠

ORDレコード
ord-0c9b52799a784be0bfb5b459fa1cf985
出典データセット
uspto-grants-2003_02
特許番号
US06515027B1

反応ノート

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