Pyridine → 4-Bromo-4'-isopropyloxybiphenyl

HRID 2078446

Reaction equation

HRID 2078446 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 200872814-Bromo-4'-isopropyloxybiphenylYield 49.5%

Reagents, catalysts & solvents 2

HCID 164827Copper oxide (CuO)CatalystHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-d3ec91c6c2514aac86d7966d1b7523e5
Source dataset
uspto-grants-2011_04
Patent number
US07928243B2

Linked notes

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