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Toluene → 1,5-Diphenylnaphthalene

HRID 909964
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인쇄 미리보기

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HRID 909964 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

HCID 534856461,5-Diphenylnaphthalene수율 60%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 80711,2-Dimethoxyethane용매

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온도
90 °C

실험 절차

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%.

후처리

  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%

출처 및 근거

ORD 기록
ord-70a514ec449d442994e92d984500aa5b
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08021574B2

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