Bromobenzene → 2-Phenylfuran

HRID 1403461Notes

Reaction equation

HRID 1403461 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:10]1([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 7961BromobenzeneHCID 62657Potassium Phosphate, TribasicHCID 2734357Furan-2-boronic acid

Product 1

HCID 5193632-PhenylfuranYield 62.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of (furan-2-yl)boronic acid (3.0 g, 26.81 mmol) in dioxane (50.0 mL) and water (1.0 mL) was added bromobenzene (2.10 g, 13.38 mmol), K3PO4 (9.3 g, 43.81 mmol) and Pd(PPh3)4 (767 mg, 0.66 mmol) with stirring for 3 h at 95° C. in an oil bath under an inert atmosphere of nitrogen. The reaction mixture was concentrated under reduced pressure to give the residue, which was purified by silica gel column chromatography (1% ethyl acetate in petroleum ether) to afford 2-phenylfuran as colorless oil (1.20 g, 62%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give the residue, which
  3. customwas purified by silica gel column chromatography (1% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-739e8501afdd4f57823d31bee8d99dc7
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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