1,3-Dibromobenzene → 3'-Bromo-2-methoxybiphenyl

HRID 45455

반응식

HRID 45455 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.[Br:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17](Br)[CH:18]=1.C(=O)(O)[O-].[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:12][C:13]1[CH:18]=[C:17]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH:16]=[CH:15][CH:14]=1

참가 물질

7

반응물 3

HCID 79271,3-DibromobenzeneHCID 516892Sodium BicarbonateHCID 27339582-Methoxyphenylboronic acid

생성물 1

HCID 186686213'-Bromo-2-methoxybiphenyl수율 190.7%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of 2-methoxyphenylboronic acid (4.3 g, 28.3 mmol), 3,5-dibromobenzene (20 g, 85.5 mmol, 3 equiv.) and bis(triphenylphosphine)palladium(II) dichloride (100 mg) in ethyleneglycol dimethylether (25 mL) and a solution of sodium bicarbonate (8.2 g, 0.098 mol) in water (140 mL) were kept at reflux under nitrogen with good stirring overnight. After cooling, the reaction mixture was partitioned between ethyl acetate (600 mL) and water (300 mL). The organic phase was washed with water (2×300 mL), dried over sodium sulfate and filtered. The solvent was removed in vacuo and the crude product was purified by chromatography on silica (150 g) with heptane (6 L) to afford pure 21 (14.2 g, 58%).

후처리

  1. temperatureat reflux under nitrogen
  2. temperatureAfter cooling
  3. customthe reaction mixture was partitioned between ethyl acetate (600 mL) and water (300 mL)
  4. washThe organic phase was washed with water (2×300 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customthe crude product was purified by chromatography on silica (150 g) with heptane (6 L)

출처 및 근거

ORD 기록
ord-da2289bbb0d444e6a1e174ec6f92aef7
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541522B2

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