Toluene → 2'-Benzyloxy-2-bromobiphenyl

HRID 269534

반응식

HRID 269534 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1Br.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>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.O.C(OCC)C.C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[Br:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

9

반응물 4

HCID 1140TolueneHCID 114141,2-DibromobenzeneHCID 11430Potassium CarbonateHCID 2773253(2-(Benzyloxy)phenyl)boronic acid

생성물 1

HCID 587309892'-Benzyloxy-2-bromobiphenyl수율 69.2%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
90 °C

실험 절차

A solution of 2-benzyloxyphenylboronic acid (4.3 g. 19.3 mmol) and 1,2-dibromobenzene (9.11 g, 4.66 ml, 38.6 mmol) in 1:1 toluene:ethanol (150 ml) was stirred under nitrogen and tetrakis(triphenylphosphine)palladium(0) (1.12 g, 0.95 mmol) and potassium carbonate (21.3 g, 154 mmol) added. The reaction was stirred at 90° C. under nitrogen for 2 hours. After cooling, diethyl ether (100 ml) and water (100 ml) were added and the organic phase separated. The aqueous phase was extracted with diethyl ether (50 ml) and the combined organic layers washed with water, dried (MgSO4) and the solvent removed in vacuo. The residue was flash chromatographed (silica gel, 5-15% CH2Cl2-isohexane) to give the title compound as a clear oil (4.53 g, 69%).

후처리

  1. temperatureAfter cooling
  2. customthe organic phase separated
  3. extractionThe aqueous phase was extracted with diethyl ether (50 ml)
  4. washthe combined organic layers washed with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customchromatographed (silica gel, 5-15% CH2Cl2-isohexane)

출처 및 근거

ORD 기록
ord-09e66ee2f0534b5281064bf3de981d67
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446222B2

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