Hydrogen Bromide → 4-Bromo-4'-chloro-3,5-diethylbiphenyl

HRID 341693ノート

反応式

HRID 341693 の反応式
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]2[CH:11]=[C:10]([CH2:12][CH3:13])[C:9](N)=[C:8]([CH2:15][CH3:16])[CH:7]=2)=[CH:4][CH:3]=1.C(#N)C.N(OCCCC)=O.[BrH:29]>[Cu]Br>[Br:29][C:9]1[C:10]([CH2:12][CH3:13])=[CH:11][C:6]([C:5]2[CH:17]=[CH:18][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:7][C:8]=1[CH2:15][CH3:16]

参加物

6

反応物 4

HCID 260Hydrogen BromideHCID 6342AcetonitrileHCID 10996Butyl nitriteHCID 594504894'-Chloro-3,5-diethylbiphen-4-ylamine

生成物 1

HCID 594504884-Bromo-4'-chloro-3,5-diethylbiphenyl

試薬・触媒・溶媒 1

HCID 24593copper(I) bromide触媒

実験手順

4′-Chloro-3,5-diethylbiphen-4-ylamine (9.6 g, 0.036 mol) is added to acetonitrile (95 ml) and stirred at room temperature until dissolution is complete. The reaction mixture is cooled to between −5° C. and 0° C., tent-butyl nitrite (5.7 ml, 0.044 mol) is added dropwise and the reaction mixture is maintained at between −5° C. and 0° C. for 30-40 minutes. The mixture is added slowly to a preheated (50° C.) suspension of copper (I) bromide (2.87 g, 0.02 mol) in hydrobromic acid (2.8 ml) and stirred at 50° C. for 10-15 minutes. The reaction mixture is cooled to room temperature, then poured into ice-cold water and extracted with ethyl acetate (3×250 ml). The organic extracts are washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to yield 4-bromo-4′-chloro-3,5-diethylbiphenyl (4.5 g).

後処理

  1. temperatureThe reaction mixture is cooled to between −5° C. and 0° C.
  2. temperaturethe reaction mixture is maintained at between −5° C. and 0° C. for 30-40 minutes
  3. stirringstirred at 50° C. for 10-15 minutes
  4. temperatureThe reaction mixture is cooled to room temperature
  5. additionpoured into ice-cold water
  6. extractionextracted with ethyl acetate (3×250 ml)
  7. washThe organic extracts are washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-44d7caa3acc1411fb58fec5a0c71aaf6
出典データセット
uspto-grants-2014_11
特許番号
US08895761B2

反応ノート

読み込み中…