Bromobenzene → 3-Phenylfuran

HRID 880498Notes

Reaction equation

HRID 880498 reaction equation
[O:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CO>[C:10]1([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 7961BromobenzeneHCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acid

Product 1

HCID 5188023-PhenylfuranYield 77.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Furan-3-boronic acid (1.0 g, 8.93 mmol), bromo benzene (1.26 g, 8.04 mmol) and sodium carbonate (1.89 g, 17.86 mmol) were dissolved in a mixture of toluene (15 mL) and methanol (5 mL) and purged with argon for 15 min. Tetrakis palladium (0) (20 mg) was added and the mixture again degassed for 15 min. The reaction was heated at 80° C. for 4 h and the resultant solids which formed were filtered and the filtrate was concentrated in vacuo to give a crude residue. Purification by flash chromatography over silica gel (100-200 mesh) using 2% ethyl acetate/petroleum ether as eluent afforded 3-phenylfuran (0.9 g, 70%).

Workup

  1. custompurged with argon for 15 min
  2. additionTetrakis palladium (0) (20 mg) was added
  3. customthe mixture again degassed for 15 min
  4. customthe resultant solids which formed
  5. filtrationwere filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customto give a crude residue
  8. customPurification by flash chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-5c8dc12b53534a8eac6fcd5b283ab151
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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