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

HRID 2405334노트

반응식

HRID 2405334 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 6114105-Bromo-2-methyl-1-benzofuran수율 62%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 7918Acetic Anhydride용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e505a6513e7c41dfb554394d67a54b49
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802864B2

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