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

HRID 1372167ノート

反応式

HRID 1372167 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[O:16][CH:15]=[CH:14][C:13]=3[CH:12]=[C:11]([CH3:18])[CH:10]=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:4]=[CH:5][C:6]([C:9]2[C:17]3[O:16][CH:15]=[CH:14][C:13]=3[CH:12]=[C:11]([CH:18]=[O:22])[CH:10]=2)=[CH:7][CH:8]=1

参加物

6

反応物 3

HCID 24450Potassium Phosphate, DibasicHCID 67184N-bromobutanimideHCID 21071796HCID 21071796、化合物

生成物 1

HCID 210717987-(4-Methoxyphenyl)-benzofuran-5-carbaldehyde収率 67%

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

To a solution of 7-(4-methoxyphenyl)-5-methyl-benzofuran (4.66 g, 19.58 mmol) in carbon tetrachloride (560 ml) was added NBS (3.83 g, 21.54 mmol) and AIBN (75 mg). The solution was brought to reflux for 4 h, cooled to room temperature, reduced by half, and the solids were filtered off. The solution was then concentrated to a yellow solid and anhydrous CH3CN (230 ml) was added. Then potassium benzeneselenite (5.34 g, 23.5 mmol), and K2HPO4 (4.09 g, 23.48 mmol) were added and then reaction was refluxed for 1.5 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 3.3 g (67%) product as a light orange solid: mp 79–80° C.; 1H NMR (300 MHz, DMSO-d6): δ 3.85 (3H, s), 7.13 (2H, d, J=8.8 Hz), 7.23 (1H, d, J=2.2 Hz), 7.88 (2H, d, J=8.8 Hz), 8.02 (1H, d, J=1.4 Hz), 8.23 (2H, m), 10.13 (1H, s); MS (ESI) m/z 253 ([M+H]+).

後処理

  1. temperatureto reflux for 4 h
  2. filtrationthe solids were filtered off
  3. concentrationThe solution was then concentrated to a yellow solid and anhydrous CH3CN (230 ml)
  4. additionwas added
  5. customreaction
  6. temperaturewas refluxed for 1.5 h after which it
  7. temperatureto cool to room temperature
  8. concentrationconcentrated under high vacuum

出典と根拠

ORDレコード
ord-2a911d1fd12f46c59ce83c2f141e3f4d
出典データセット
uspto-grants-2007_01
特許番号
US07157491B2

反応ノート

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