Ethanol → Ethyl-2-fluoro-4-iodo-phenyl acetate

HRID 51628ノート

反応式

HRID 51628 の反応式
FC([I:12])(C1C=CC=CC=1)C(O)=O.[F:13][C:14]1[CH:19]=[C:18](I)[CH:17]=[CH:16][C:15]=1[CH2:21][C:22](O)=O.S(=O)(=O)(O)O.[OH2:30].[CH2:31]([OH:33])[CH3:32]>C1C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[C:31]([O:33][C:19]1[CH:18]=[CH:17][C:16]([I:12])=[C:15]([CH2:21][CH3:22])[C:14]=1[F:13])(=[O:30])[CH3:32]

参加物

9

反応物 5

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 222403932-(2-Fluoro-4-iodophenyl)acetic acidHCID 225689092-Fluoro-iodo-phenyl acetic acid

生成物 1

HCID 69548701Ethyl-2-fluoro-4-iodo-phenyl acetate収率 73%

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2-fluoro-iodo-phenyl acetic acid (Intermediate 3, 1.75 g, 6.22 mmol) in ethanol (50 mL) and benzene (100 mL) was treated with concentrated sulfuric acid (1.4 mL) and heated at reflux overnight using a Dean-Stark water trap. The volatiles were distilled off in vacuo and the residue was diluted with water and diethyl ether. The phases were separated and the organic phase was washed with saturated aqueous sodium bicarbonate (×1), water (×1) and brine (×1), dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 5%-10% ethyl acetate in hexane as the eluent to afford the title compound as a pale yellow solid (1.4 g, 73%).

後処理

  1. temperatureheated
  2. temperatureat reflux overnight
  3. distillationThe volatiles were distilled off in vacuo
  4. additionthe residue was diluted with water and diethyl ether
  5. customThe phases were separated
  6. washthe organic phase was washed with saturated aqueous sodium bicarbonate (×1), water (×1) and brine (×1)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto afford an oil which

出典と根拠

ORDレコード
ord-edd8c092074845fe99a6ffd258ced69b
出典データセット
uspto-grants-2004_03
特許番号
US06713647B2

反応ノート

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