Sodium Hydroxide → 5-Bromo-2-methyl-1-benzofuran

HRID 2405334ノート

反応式

HRID 2405334 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]([CH3:13])[C:10](O)=O)=[C:4](C=O)[CH:3]=1.C([O-])(=O)C.[Na+].[OH-].[Na+]>C(OC(=O)C)(=O)C.C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:8][C:9]([CH3:10])=[CH:13][C:6]=2[CH:7]=1

参加物

7

反応物 3

HCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 33670222-(4-Bromo-2-formylphenoxy)propanoic acid

生成物 1

HCID 6114105-Bromo-2-methyl-1-benzofuran収率 62%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 7918Acetic Anhydride溶媒

実験手順

A solution of 2-[(4-bromo-2-formylphenyl)oxy]propanoic acid (5.08 mmol) in acetic anhydride (6 mL) was treated with sodium acetate (15.25 mmol). The resulting solution was heated to reflux and stirred overnight. The brown reaction solution was allowed to cool to room temperature, and was diluted with toluene (10 mL). The solution was then treated with 1N aq NaOH (10 mL) and was stirred at room temperature for 20 min. The solution was then further diluted with water (50 mL) and was extracted using ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting brown residue was purified by flash chromatography (hexanes), affording the title compound as a clear oil (660 mg, 62% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.73 (d, J=2.02 Hz, 1H) 7.47 (d, J=8.59 Hz, 1H) 7.35 (dd, J=8.72, 2.15 Hz, 1H) 6.58 (s, 1H) 2.45 (d, J=1.01 Hz, 3H).

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. stirringwas stirred at room temperature for 20 min
  4. extractionwas extracted
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting brown residue was purified by flash chromatography (hexanes)

出典と根拠

ORDレコード
ord-e505a6513e7c41dfb554394d67a54b49
出典データセット
uspto-grants-2014_08
特許番号
US08802864B2

反応ノート

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