4-Iodoanisole → 1-(4'-Methoxy-2-nitro-[1,1'-biphenyl]-4-yl)ethanone

HRID 918127

反応式

HRID 918127 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21]>[Cu]>[C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)=[C:12]([N+:20]([O-:22])=[O:21])[CH:13]=1)(=[O:19])[CH3:18]

参加物

4

反応物 2

HCID 696764-IodoanisoleHCID 877371-(4-Bromo-3-nitrophenyl)ethan-1-one

生成物 1

HCID 189566161-(4'-Methoxy-2-nitro-[1,1'-biphenyl]-4-yl)ethanone

試薬・触媒・溶媒 1

HCID 23978Copper触媒

反応条件

温度
80 °C

実験手順

A stirred mixture of 4-iodoanisole (174.5 g.), 4'-bromo-3'-nitroacetophenone (162.5 g.) and copper powder (144 g.) was heated at 80°C. for 5 hours and the temperature was then gradually raised during 4 hours to 110°C. The stirred mixture was maintained at 110°C. for a further period of 3 days. The reaction mixture was cooled to room temperature and extracted with methylene dichloride. The extract was filtered and the filtrate evaporated under reduced pressure to remove methylene dichloride. The residue was distilled in vacuo to give the product, b.p. 200° - 210°C./0.6 mm., which solidified on cooling. This product was recrystallized from methanol to give 4-acetyl-4'-methoxy-2-nitrobiphenyl, m.p. 127° - 129°C. (novel intermediate A).

後処理

  1. temperaturethe temperature was then gradually raised during 4 hours to 110°C
  2. temperatureThe stirred mixture was maintained at 110°C. for a further period of 3 days
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionextracted with methylene dichloride
  5. filtrationThe extract was filtered
  6. customthe filtrate evaporated under reduced pressure
  7. customto remove methylene dichloride
  8. distillationThe residue was distilled in vacuo
  9. customto give the product, b.p. 200° - 210°C./0.6 mm
  10. temperatureon cooling
  11. customThis product was recrystallized from methanol

出典と根拠

ORDレコード
ord-b40cd95393ac415f8610004776c1cfed
出典データセット
uspto-grants-1976_07
特許番号
US03969402

関連ノート

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