Potassium Phosphate, Dibasic → 5-(4-Methoxy-phenyl)-benzofuran-7-carbaldehyde

HRID 1372162노트

반응식

HRID 1372162 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH3:18])[C:12]3[O:16][CH:15]=[CH:14][C:13]=3[CH:17]=2)=[CH:5][CH:4]=1.C1C(=O)N(Br)C(=[O:22])C1.OP([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:18]=[O:22])[C:12]3[O:16][CH:15]=[CH:14][C:13]=3[CH:17]=2)=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 24450Potassium Phosphate, DibasicHCID 67184N-bromobutanimideHCID 210717895-(4-Methoxyphenyl)-7-methyl-benzofuran

생성물 1

HCID 210717905-(4-Methoxy-phenyl)-benzofuran-7-carbaldehyde수율 50.1%

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매HCID 5943Carbon Tetrachloride용매

실험 절차

To a solution of 5-(4-methoxyphenyl)-7-methyl-benzofuran (1.60 g, 2.83 g 1:1 ratio with 4-methoxy-biphenyl 6.72 mmol) in carbon tetrachloride (190 ml) was added NBS (1.32 g, 7.40 mmol) and AIBN (50 mg). The solution was brought to reflux for 2 h, cooled to room temperature, and the solids were filtered off. The solution was then concentrated and anhydrous CH3CN (80 ml) was added. Then potassium benzeneselenite (2.14 g, 9.41 mmol), and K2HPO4 (1.17 g, 6.72 mmol) were added and then reaction was heated to reflux for 1 h after which it was allowed to cool to room temperature. The solution was then passed through a silica plug and concentrated under high vacuum. Chromatography (100% CH2Cl2) afforded 850 mg (50%) product as a white solid: mp 94–95° C.; 1H NMR (300 MHz, DMSO-d6): δ 3.82 (3H, s), 7.08 (2H, d, J=8.8 Hz), 7.14 (1H, d, J=2.2 Hz), 7.71 (2H, d, J=8.8 Hz), 8.10 (1H, d, J=1.9 Hz), 8.21 (1H, d, J=2.2 Hz), 8.25 (1H, d, J=1.9 Hz), 10.37 (1H, s); MS (ESI) m/z 253 ([M+H]+).

후처리

  1. temperatureto reflux for 2 h
  2. filtrationthe solids were filtered off
  3. concentrationThe solution was then concentrated
  4. additionanhydrous CH3CN (80 ml) was added
  5. customreaction
  6. temperaturewas heated
  7. temperatureto reflux for 1 h after which it
  8. temperatureto cool to room temperature
  9. concentrationconcentrated under high vacuum

출처 및 근거

ORD 기록
ord-af8f9388d9d640ec8835d587aa4c0212
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157491B2

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