Toluene → 1,6-Diphenylpyrene

HRID 530183ノート

反応式

HRID 530183 の反応式
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:34]1(C)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>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.O1CCCC1>[C:19]1([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[CH:11]=[CH:10][C:9]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 176470Pyrene, 1,6-Dibromo-

生成物 1

HCID 591334031,6-Diphenylpyrene

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Under an argon atmosphere, 15.0 g of 1,6-dibromopyrene, 13.2 g of phenylboronic acid, 1.9 g of tetrakis(triphenylphosphine)palladium (0) [Pd(PPh3)4], 27.8 g of sodium carbonate (130 mL of clean water), toluene and tetrahydrofuran were placed into a flask, and the resulting mixture was allowed to react at 90° C. for 7 hours. After cooling, the reaction solution was filtered, and solids obtained were washed with methanol and clean water. Further, the solids were purified by silica gel chromatography (heated toluene). The resulting crude product which was obtained by a concentration was re-crystallized from toluene, followed by drying under a reduced pressure, whereby white solids of 1,6-diphenylpyrene (11.8 g) were obtained.

後処理

  1. customto react at 90° C. for 7 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction solution was filtered
  4. customsolids obtained
  5. washwere washed with methanol and clean water
  6. customFurther, the solids were purified by silica gel chromatography (heated toluene)

出典と根拠

ORDレコード
ord-67f7b26c2ed24c3ebedb3ecc71d7e8b7
出典データセット
uspto-grants-2016_05
特許番号
US09353027B2

反応ノート

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