1-Bromo-4-fluorobenzene → 2-(4-Fluorophenyl)furan

HRID 1403482Notes

Reaction equation

HRID 1403482 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1B(O)O.[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>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]2[O:9][CH:13]=[CH:12][CH:11]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 99931-Bromo-4-fluorobenzeneHCID 62657Potassium Phosphate, TribasicHCID 2734357Furan-2-boronic acid

Product 1

HCID 116152232-(4-Fluorophenyl)furanYield 90%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
90 °C

Procedure

To a solution of 1-bromo-4-fluorobenzene (3.0 g, 17.14 mmol) in dioxane (100.0 mL) and water (3.0 mL) was added (furan-2-yl)boronic acid (5.76 g, 51.48 mmol), K3PO4 (10.76 g, 50.69 mmol) and Pd(PPh3)4 (980 mg, 0.85 mmol) with stirring for 2 h at 90° C. in an oil bath maintained under an inert atmosphere of nitrogen. The reaction mixture was concentrated under reduced pressure to give the residue, which was purified via silica gel chromatography (1% ethyl acetate in petroleum ether) to afford 2-(4-fluorophenyl)furan as colorless oil (2.5 g, 90%).

Workup

  1. temperaturemaintained under an inert atmosphere of nitrogen
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give the residue, which
  4. customwas purified via silica gel chromatography (1% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-7ec381d3e5c243c1a50265fe8bef056a
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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