Toluene → [3'-(3,6-Diphenylcarbazol-9-yl)biphenyl-3-yloxy]methane

HRID 1502190

反応式

HRID 1502190 の反応式
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:20]3[CH:19]=[CH:18][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[C:12]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:13]=3)[CH:5]=[CH:6][CH:7]=1.[CH3:33][O:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C(Cl)Cl.C1C=CC([P]([Pd]([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)=CC=1.C(O)C>[C:27]1([C:12]2[CH:11]=[CH:10][C:9]3[N:8]([C:4]4[CH:5]=[C:6]([C:37]5[CH:38]=[CH:39][CH:40]=[C:35]([O:34][CH3:33])[CH:36]=5)[CH:7]=[CH:2][CH:3]=4)[C:20]4[C:15]([C:14]=3[CH:13]=2)=[CH:16][C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:18][CH:19]=4)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

9

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 581422319-(3-bromophenyl)-3,6-diphenyl-9H-Carbazole

生成物 1

HCID 66717069[3'-(3,6-Diphenylcarbazol-9-yl)biphenyl-3-yloxy]methane収率 85.4%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

The obtained 9-(3-bromophenyl)-3,6-diphenylcarbazole (3.20 g, 6.75 mmol), 3-methoxyphenylboronic acid (1.54 g, 10.1 mmol) and tetrakis(triphenylphosphine)palladium (0.124 g) were added to a solvent mixture of toluene (30 mL) and ethanol (10 mL). Then, an aqueous solution of sodium carbonate (37.3 g) in distilled water (90 mL) was added the mixture. The resultant mixture was refluxed for 9 hours in a nitrogen atmosphere and then cooled to room temperature. The obtained mixture was diluted with methylene chloride and the insoluble matter was removed through filtration. The organic layer was washed with water and separated. The solvent was evaporated under reduced pressure. The residue was purified through silica gel column chromatography using as an eluent a solvent mixture of methylene chloride/hexane (2/3 by volume), to thereby obtain 2.89 g of [3′-(3,6-diphenylcarbazol-9-yl)biphenyl-3-yloxy]methane.

後処理

  1. customthe insoluble matter was removed through filtration
  2. washThe organic layer was washed with water
  3. customseparated
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography
  6. additiona solvent mixture of methylene chloride/hexane (2/3 by volume)

出典と根拠

ORDレコード
ord-31d2d8947f3d4766817a5f37423f0bd2
出典データセット
uspto-grants-2015_12
特許番号
US09206202B2

関連ノート

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