1,2-Dibromobenzene → 3-(2-Bromophenyl)-9-phenyl-9H-carbazole

HRID 1808690ノート

反応式

HRID 1808690 の反応式
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1Br>O1CCOCC1.C(OCCO)C.C(=O)([O-])[O-].[Na+].[Na+].C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:16]1[CH:17]=[CH:18][C:19]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

参加物

7

反応物 2

HCID 114141,2-DibromobenzeneHCID 513584509-Phenyl-9H-carbazole-3-boronic acid

生成物 1

HCID 669295403-(2-Bromophenyl)-9-phenyl-9H-carbazole

試薬・触媒・溶媒 4

HCID 178420553HCID 178420553、化合物触媒HCID 8076Glycol monoethyl ether溶媒HCID 10340Sodium Carbonate溶媒HCID 312751,4-Dioxane溶媒

実験手順

1.1 g (1 mmol) of tetrakis(triphenylphosphino)palladium(0) are added to a mixture of 28.7 g (100 mmol) of N-phenylcarbazole-3-boronic acid, 36.1 ml (300 mmol) of 1,2-dibromobenzene in 150 ml of dioxane, 100 ml of 2-ethoxyethanol and 250 ml of 2 N sodium carbonate solution, and the mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, 500 ml of toluene are added, and the mixture is washed three times with 500 ml of water, dried over magnesium sulfate, filtered through silica gel and then freed from toluene and excess 1,2-dibromobenzene in vacuo. The residue is washed by stirring three times with hot ethanol. Yield: 26.7 g (67 mmol), 67.1%, purity 97% according to

後処理

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. addition500 ml of toluene are added
  6. washthe mixture is washed three times with 500 ml of water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered through silica gel
  9. washThe residue is washed

出典と根拠

ORDレコード
ord-3f3fc7a08fba4a14a48ca9433b59d217
出典データセット
uspto-grants-2013_01
特許番号
US08361638B2

反応ノート

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