Benzene, 1-bromo-3-iodo- → 2-(3-bromophenyl)furan

HRID 2066386Notes

Reaction equation

HRID 2066386 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.C([Sn](CCCC)(CCCC)[C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)CCC.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:1][C:2]1[CH:3]=[C:4]([C:14]2[O:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11561Benzene, 1-bromo-3-iodo-HCID 80271Tri-o-tolylphosphineHCID 43936882-(Tributylstannyl)furan

Product 1

HCID 106091182-(3-bromophenyl)furan

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

1-Bromo-3-iodobenzene (3.0 g), tris(dibenzylideneacetone)dipalladium(0) (1.22 g), tributyl(furan-2-yl)tin (3.34 ml), and tri(o-tolyl)phosphine (807 mg) were dissolved in dioxane (30 ml), and the solution was stirred at room temperature for 20 hours, at 35° C. for 6 hours, at 45° C. for 19 hours, and at 55° C. for 5 hours and 30 minutes. The reaction mixture was filtered through Celite, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (NH-form, hexane) to obtain the title compound (1.40 g).

Workup

  1. waitat 55° C. for 5 hours
  2. custom30 minutes
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (NH-form, hexane)

Sources & evidence

ORD record
ord-59f99089eb154c02922740a4e714ff08
Source dataset
uspto-grants-2012_10
Patent number
US08293715B2

Reaction notes

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