Pyridine → 4-Bromo-4'-isopropyloxybiphenyl

HRID 2078446

반응식

HRID 2078446 반응식
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8](O)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[Br:12][C:13]1[CH:18]=[CH:17][C:16](Br)=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].N1C=CC=CC=1>[O-2].[Cu+2].C(Cl)Cl>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:16]2[CH:17]=[CH:18][C:13]([Br:12])=[CH:14][CH:15]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 1049PyridineHCID 78041,4-DibromobenzeneHCID 11430Potassium CarbonateHCID 820014-Isopropoxyphenol

생성물 1

HCID 200872814-Bromo-4'-isopropyloxybiphenyl수율 49.5%

시약·촉매·용매 2

HCID 164827Copper oxide (CuO)촉매HCID 6344Dichloromethane용매

실험 절차

To a mixture of Example 1A (505 mg, 3.31 mmol), 1,4-dibromobenzene (2.34 g, 9.92 mmol.), K2CO3 (960 mg, 6.87 mmol) and pyridine (20 mL) at 80° C. was added Cu(II) oxide (650 mg, 8.17 mmol). After the addition, the mixture was refluxed vigorously for 20 h. After cooling, methylene chloride was added and the mixture was filtered through Celite. The filtrate was concentrated to dryness. The residue was dissolved in ether, which was washed with 10% HCl (2×), 1N NaOH (2×), brine (1×), dried over MgSO4, and concentrated to dryness. The residue was purified on silica gel eluting with hexane and ethyl acetate gradient to give the desired product as a white solid (477 mg, 47%).

후처리

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed vigorously for 20 h
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite
  5. concentrationThe filtrate was concentrated to dryness
  6. dissolutionThe residue was dissolved in ether
  7. washwhich was washed with 10% HCl (2×), 1N NaOH (2×), brine (1×)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated to dryness
  10. customThe residue was purified on silica gel eluting with hexane and ethyl acetate gradient

출처 및 근거

ORD 기록
ord-d3ec91c6c2514aac86d7966d1b7523e5
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928243B2

연결된 노트

불러오는 중…