Tetrahydrofuran → 2-Bromo-6-phenylpyridine

HRID 1901119Notes

Reaction equation

HRID 1901119 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[Li][CH2:10][CH2:11][CH2:12][CH3:13].[CH2:14]1COC[CH2:15]1>CCCCCC.[Cl-].[Cl-].[Zn+2]>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 122742,6-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 5686792-Bromo-6-phenylpyridine

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8058HexaneSolvent

Procedure

To a solution of 2,6-dibromopyridine (2 g) in THF (100 mL) at -100° C. was added n-BuLi (6 mL of a 1.4M solution in hexane) over 10 min. After stirring for 20 min., ZnCl2 (17 mL of a 0.5M solution in THF) was added. The cold bath was removed and after 40 min., iodobenzene (0.94 mL) and tetrakis (triphenylphosphine) palladium (390 mg) were added and the mixture stirred at r.t. for 20 h. Ethyl acetate was added and the organics were washed with NaHCO3, H2O and brine, dried (MgSO4) and concentrated. Chromatography (silica gel; hexane/EtOAc (97:3)) provided the title compound as a solid.

Workup

  1. customThe cold bath was removed and after 40 min.
  2. additioniodobenzene (0.94 mL) and tetrakis (triphenylphosphine) palladium (390 mg) were added
  3. stirringthe mixture stirred at r.t. for 20 h
  4. additionEthyl acetate was added
  5. washthe organics were washed with NaHCO3, H2O and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dcfec37b63e8413287248b86a321059b
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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