Acetic Anhydride → 5-Bromo-3-methyl-1-benzofuran

HRID 2405327ノート

反応式

HRID 2405327 の反応式
[C:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:12]C(O)=O)(=O)[CH3:2].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C>[Br:10][C:8]1[CH:7]=[CH:6][C:5]2[O:11][CH:12]=[C:1]([CH3:2])[C:4]=2[CH:9]=1

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 192613632-(2-Acetyl-4-bromophenoxy)acetic acid

生成物 1

HCID 123375005-Bromo-3-methyl-1-benzofuran

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
140 °C

実験手順

A solution of [(2-acetyl-4-bromophenyl)oxy]acetic acid (1.648 mmol) in acetic acid (2.075 mL) was treated with sodium acetate (9.89 mmol) and acetic anhydride (21.42 mmol). The reaction solution was heated with stirring to 140° C. for 3.5 h. Analysis by LCMS showed a major product that did not ionize, and consumption of starting material. The mixture was diluted with water and ethyl acetate and was washed with 1N aq NaOH until the aqueous phase was basic (pH˜12). The mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to an oil in vacuo. No further purification was carried out. 1H NMR (400 MHz, chloroform-d) δ ppm 7.67 (d, J=1.77 Hz, 1H) 7.38-7.45 (m, 2H) 7.32-7.38 (m, 1H) 2.24 (d, J=1.26 Hz, 3H).

後処理

  1. temperatureThe reaction solution was heated
  2. customconsumption of starting material
  3. additionThe mixture was diluted with water and ethyl acetate
  4. washwas washed with 1N aq NaOH until the aqueous phase
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to an oil in vacuo
  10. customNo further purification

出典と根拠

ORDレコード
ord-506f06d9d6864c09b8c3688aa30504ef
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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