Iodobenzene → 2-Bromo-9-phenyl-9H-carbazole

HRID 1473733ノート

反応式

HRID 1473733 の反応式
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:8][C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH:10]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:8][C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:11]=2[CH:10]=1

参加物

7

反応物 4

HCID 11575IodobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 127170892-Bromo-9H-carbazoleHCID 23676156Sodium t-butoxide

生成物 1

HCID 668380442-Bromo-9-phenyl-9H-carbazole収率 37.3%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

30.51 g (149.56 mmol) of iodobenzene, 18.32 g (74.78 mmol) of 2-bromo-9H-carbazole, 14.37 g (149.56 mmol) of sodium t-butoxide, and 1.81 ml (7.48 mmol) of tritertbutylphosphine were dissolved in 300 ml of toluene, and 0.68 g (0.75 mmol) of Pd2(dba)3 was added thereto, and refluxed and agitated for 12 hours. After the reaction was finished, extraction was performed by dichloromethane, filtering was performed by silica gel, and the column was used at a ratio of hexane:MC=9:1 (v/v) to obtain 8.99 g of 2-bromo-9-phenylcarbazole (yield 37%).

後処理

  1. temperaturerefluxed
  2. extractionextraction
  3. filtrationfiltering

出典と根拠

ORDレコード
ord-42b2fd1ef53a45db89acabe54edde7d6
出典データセット
uspto-grants-2015_04
特許番号
US09017829B2

反応ノート

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