Benzofuran → 2-(4-Methoxyphenyl)benzofuran

HRID 1387048Notes

Reaction equation

HRID 1387048 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Li]CCCC.I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23]>CCOCC.N1C=CC=CC=1>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][C:20]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)=[CH:21][CH:16]=1

Participants

6

Reactant 3

HCID 9223BenzofuranHCID 68257o-IodoanisoleHCID 178418339Butyllithium

Product 1

HCID 107278342-(4-Methoxyphenyl)benzofuranYield 50.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
110 °C

Procedure

A solution of 46.0 g (0.39 mole) of benzofuran in 100 mL of Et2O was treated with 0.40 mol (1.6 M in hexanes) of n-BuLi at such a rate as to keep the reaction temperature below 25° C. The mixture was stirred for 15 min and was added to a 10° C. solution of 57.2 g (0.40 mole) of CuBr in 100 mL of Et2O at a rate so as to keep the reaction temperature below 10° C. The mixture was allowed to reach room temperature over 0.5 h and was treated with a solution of 93.6 g of iodoanisole in 300 mL of pyridine. The mixture was heated to 110° C. for 3 h, allowing the Et2O to boil off. The reaction mixture was concentrated in vacuo and the residue was dissolved in 3 L of EtOAc. The organic layer was washed several times with 2 N aqueous HCl and once with H2O, dried over MgSO4, and filtered. Concentration in vacuo afforded a residue which was recrystallized from MeOH to afford 44.5 g of the title compound as a solid.

Workup

  1. customthe reaction temperature below 25° C
  2. customthe reaction temperature below 10° C
  3. waitto reach room temperature over 0.5 h
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. dissolutionthe residue was dissolved in 3 L of EtOAc
  6. washThe organic layer was washed several times with 2 N aqueous HCl
  7. dry with materialonce with H2O, dried over MgSO4
  8. filtrationfiltered
  9. concentrationConcentration in vacuo
  10. customafforded a residue which
  11. customwas recrystallized from MeOH

Sources & evidence

ORD record
ord-8649c6ca20c842158983d2f348d34ceb
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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