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

HRID 558984

반응식

HRID 558984 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 46853502-(Furan-2-yl)aniline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-940efed197184e388209bc0404d88a2d
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063038B2

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