o-Chloranil → 8,9-Dihydrocyclopenta[def]phenanthrene

HRID 505844

反応式

HRID 505844 の反応式
Br[C:2]1[CH:15]=[C:14]2[CH2:16][C:11]3[C:12]4[C:13]2=[C:4]([CH2:5][CH2:6][C:7]=4[CH:8]=[C:9](Br)[CH:10]=3)[CH:3]=1.C1(Cl)C(Cl)=C(Cl)C(=O)C(=O)C=1Cl>C1(C)C(C)=CC=CC=1>[CH:3]1[C:4]2[CH2:5][CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[CH2:16][C:14]([C:13]=2[C:12]=34)=[CH:15][CH:2]=1

参加物

4

反応物 2

HCID 73252o-ChloranilHCID 125243672,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene

生成物 1

HCID 6057498,9-Dihydrocyclopenta[def]phenanthrene収率 147.4%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

2,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene (4.45 g, 12.7 mmol) in a 250 ml round bottom flask was dissolved with xylene, and o-chloranil (4.15 g) was added thereto at room temperature. The reaction mixture was heated and refluxed in an oil bath for 72 hours. After the reaction was terminated, the reaction solution was cooled and concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (mobile solvent: n-hexane) to give a compound 1 (3.6 g, 81%).

後処理

  1. additionwas added
  2. customat room temperature
  3. temperatureThe reaction mixture was heated
  4. temperaturerefluxed in an oil bath for 72 hours
  5. customAfter the reaction was terminated
  6. temperaturethe reaction solution was cooled
  7. concentrationconcentrated under a reduced pressure
  8. customThe residue was purified by silica gel column chromatography (mobile solvent: n-hexane)

出典と根拠

ORDレコード
ord-9f9ac81cc2ca47fa9b522917d7a49279
出典データセット
uspto-grants-2010_08
特許番号
US07781579B2

関連ノート

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