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1,2-Dibromoethane → 9,9-Bis(3-bromophenyl)-9H-fluorene

HRID 1483879
ノート
印刷プレビュー

反応式

HRID 1483879 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.BrCCBr.[Mg].[Br:19][C:20]1[CH:21]=[C:22]([C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Br:34])[CH:29]=2)=O)[CH:23]=[CH:24][CH:25]=1>C1COCC1.COCCOC.C1(C)C=CC=CC=1>[Br:19][C:20]1[CH:21]=[C:22]([C:26]2([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([Br:34])[CH:29]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:8]3[C:13]2=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:23]=[CH:24][CH:25]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 78391,2-DibromoethaneHCID 163292-BromobiphenylHCID 5462224MagnesiumHCID 12731928Bis(3-bromophenyl)methanone

生成物 1

HCID 226304269,9-Bis(3-bromophenyl)-9H-fluorene

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒
HCID 8028
Tetrahydrofuran
溶媒
2 回
HCID 80711,2-Dimethoxyethane溶媒

実験手順

62.9 g (270 mmol) of 2-bromobiphenyl mixed with 400 ml of THF, 550 ml of toluene, 45 ml of 1,2-dimethoxyethane and 2.6 ml of 1,2-dibromoethane are reacted with 6.6 g (250 mmol) of magnesium to give the corresponding Grignard compound. A solution of 60.0 g (176 mmol) of bis(3-bromophenyl) ketone in 600 ml of THF is added dropwise to the cooled Grignard solution. When the addition is complete, the reaction mixture is heated under reflux for 4 h, the solvent is then removed in vacuo, the residue is dissolved in 700 ml of glacial acetic acid, 10 ml of hydrogen bromide in 30% glacial acetic acid are added, and the mixture is heated under reflux for 6 h. After cooling with stirring, the precipitated solid is filtered off with suction, washed twice with 200 ml of glacial acetic acid each time and three times with 300 ml of ethanol each time and then dried in vacuo. Yield: 69.0 g (145 mmol), 82.1%, 99% pure according to 1H-NMR.

後処理

  1. customto give the corresponding Grignard compound
  2. additionWhen the addition
  3. temperaturethe reaction mixture is heated
  4. temperatureunder reflux for 4 h
  5. customthe solvent is then removed in vacuo
  6. dissolutionthe residue is dissolved in 700 ml of glacial acetic acid
  7. addition10 ml of hydrogen bromide in 30% glacial acetic acid are added
  8. temperaturethe mixture is heated
  9. temperatureunder reflux for 6 h
  10. temperatureAfter cooling
  11. filtrationthe precipitated solid is filtered off with suction
  12. washwashed twice with 200 ml of glacial acetic acid each time and three times with 300 ml of ethanol each time
  13. customdried in vacuo

出典と根拠

ORDレコード
ord-7fce24a651ee49c0bfa4055cbc1c9a2e
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09416310B2

反応ノート

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