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Toluene → 1,5-Diphenylnaphthalene

HRID 909964
ノート
印刷プレビュー

反応式

HRID 909964 の反応式
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[C:12](OS(C(F)(F)F)(=O)=O)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)(=O)=O.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:36]1(C)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(=O)([O-])[O-].[Na+].[Na+]>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(COC)OC>[C:27]1([C:7]2[C:16]3[C:11](=[C:12]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 149765711,5-Naphthalenebis(trifluoromethanesulfonate)

生成物 1

HCID 534856461,5-Diphenylnaphthalene収率 60%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

Under an argon gas atmosphere, 49.0 g (106.1 mmol) of 5-{[(trifluoromethyl) sulfonyl]oxy}naphthyl trifluoromethanesulfonate, 28.5 g (233.3 mmol) of phenylboronic acid, 4.90 g (4.24 mmol) of tetrakis(triphenylphosphine)palladium(0), 200 ml of toluene, 100 ml of dimethoxyethane and 320 ml of 2M sodium carbonate solution were mixed, and stirred for 24 hours at 90 degrees C. After the reaction in the mixture was over, the mixture experienced filtration, through which aqueous phase thereof was eliminated. After organic phase thereof was cleansed by water and dried with magnesium sulfate, the solvent was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 18.0 g of 1.5-diphenylnaphthalene was obtained with an yield of 60%.

後処理

  1. customAfter the reaction in the mixture
  2. filtrationfiltration
  3. dry with materialdried with magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customwas obtained with an yield of 60%

出典と根拠

ORDレコード
ord-70a514ec449d442994e92d984500aa5b
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08021574B2

反応ノート

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