Sodium Carbonate → 2-(Furan-2-yl)aniline

HRID 558984Notes

Reaction equation

HRID 558984 reaction equation
Br[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 119922-BromoanilineHCID 2734357Furan-2-boronic acid

Product 1

HCID 46853502-(Furan-2-yl)aniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromoaniline (137 mg, 0.80 mmol) in THF (4.0 ml) was added 2-furanboronic acid (89 mg, 0.80 mmol), tetrakis-(triphenylphosphine)palladium (0) (92 mg, 0.08 mmol) and sodium carbonate solution (2M, 2.0 ml, 4.0 mmol). The mixture was heated in a sealed tube using a microwave reactor (20 W) at 130° C. for 25 min. This procedure was carried out 5 times and the reaction mixtures were combined. The mixture was separated and the aqueous layer extracted with EtOAc. The combined organic layers were dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 85:15) to give a brown oil; yield 211 mg, 33%.

Workup

  1. temperatureThe mixture was heated in a sealed tube
  2. customat 130° C.
  3. customfor 25 min
  4. customthe reaction mixtures
  5. customThe mixture was separated
  6. extractionthe aqueous layer extracted with EtOAc
  7. customThe combined organic layers were dried
  8. customevaporated in vacuo
  9. customThe residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 85:15)
  10. customto give a brown oil

Sources & evidence

ORD record
ord-940efed197184e388209bc0404d88a2d
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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