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

HRID 395023노트

반응식

HRID 395023 반응식
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]

참가 물질

9

반응물 5

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

생성물 1

HCID 69548701Ethyl-2-fluoro-4-iodo-phenyl acetate수율 73%

시약·촉매·용매 3

HCID 241Benzene용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-88c2ae33f32f404daa495e6e6624f5b3
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06603019B2

반응 노트

불러오는 중…