Sodium Carbonate → 3-(1-Naphthyl)-1-bromobenzene

HRID 1045296노트

반응식

HRID 1045296 반응식
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:14][C:15]1[CH:16]=[C:17](I)[CH:18]=[CH:19][CH:20]=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.C1(C)C=CC=CC=1>[Br:14][C:15]1[CH:20]=[C:19]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 2545321-Naphthaleneboronic acid

생성물 1

HCID 221380473-(1-Naphthyl)-1-bromobenzene수율 76%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

Under an argon gas atmosphere, 200.0 g (1.163 mol) of 1-naphthaleneboronic acid, 329.0 g (1.163 mol) of 3-bromoiodobenzene, 26.9 g (23.3 mmol) of tetrakis(triphenylphosphine)palladium(0), 3.7 L of toluene and 1.74 L of aqueous solution of 2M sodium carbonate were added together, and stirred while being refluxed for 24 hours. After the reaction was over, the mixture experienced filtration, through which aqueous phase thereof was eliminated. After organic phase thereof was washed by water and dried with magnesium sulfate, the toluene was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 250 g of 1-(3-bromophenyl)naphthalene was obtained at an yield of 76%.

후처리

  1. temperaturewhile being refluxed for 24 hours
  2. filtrationfiltration
  3. washAfter organic phase thereof was washed by water
  4. dry with materialdried with magnesium sulfate
  5. distillationthe toluene was distilled away under reduced pressure
  6. customwas obtained at an yield of 76%

출처 및 근거

ORD 기록
ord-61243ac04cf94fc591cd6bc1aeba5734
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08568903B2

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