Pyridine → 4-Bromo-4'-isopropyloxybiphenyl

HRID 2078446

反応式

HRID 2078446 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 200872814-Bromo-4'-isopropyloxybiphenyl収率 49.5%

試薬・触媒・溶媒 2

HCID 164827Copper oxide (CuO)触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-d3ec91c6c2514aac86d7966d1b7523e5
出典データセット
uspto-grants-2011_04
特許番号
US07928243B2

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