Ethanol → Ethyl 2-fluoro-4-iodobenzoate

HRID 635557

反応式

HRID 635557 の反応式
[F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12](O)[CH3:13].S(=O)(=O)(O)O>>[F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:12][CH3:13])=[O:5]

参加物

4

反応物 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27745162-Fluoro-4-iodobenzoic acid2 回

生成物 1

HCID 18761561Ethyl 2-fluoro-4-iodobenzoate

反応条件

温度
90 °C

実験手順

To a solution of 2.5 g (27.0 mmol) of 2-fluoro-4-iodobenzoic acid (Compound B) in 11 mL (8.6 g, 187.5 mmol) of ethanol was added 0.3 mL of c. sulfuric acid. The reaction mixture was heated to reflux in an oil bath (90° C.) for 1.75 hours, fitted with a short path distillation apparatus, distilled and then allowed to cool to ambient temperature. The reaction mixture was extracted and partitioned between pentane and water and the layers were separated. The aqueous phase was washed with pentane and the organic phases were combined. The combined organic phase was washed sequentially with sat. NaHCO3 (aq.) solution, water and brine, dried over MgSO4, filtered and concentrated in vacuo to a purple oil. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) gave the title compound as an orange oil. PMR (CDCl3): δ 1.39 (3 H, t, J=7.1 Hz), 4.39 (2 H, q, J=7.1 Hz), 7.52-7.67 (3 H, m).

後処理

  1. temperatureThe reaction mixture was heated
  2. customfitted with a short path distillation apparatus
  3. distillationdistilled
  4. temperatureto cool to ambient temperature
  5. extractionThe reaction mixture was extracted
  6. custompartitioned between pentane and water
  7. customthe layers were separated
  8. washThe aqueous phase was washed with pentane
  9. washThe combined organic phase was washed sequentially with sat. NaHCO3 (aq.) solution, water and brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo to a purple oil
  13. customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-2589b79ccfaa44fe8fcf983660f1bf49
出典データセット
uspto-grants-2001_02
特許番号
US06187950B1

関連ノート

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