2,3-Difluorophenol → (E)-3-(2,3-difluoro-phenoxy)-but-2-enoic acid ethyl ester

HRID 19230

반응식

HRID 19230 반응식
CC(C)([O-])C.[K+].[F:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=1[OH:15].[CH2:16]([O:18][C:19](=[O:24])[CH:20]=[C:21](Cl)[CH3:22])[CH3:17]>O1CCCC1>[CH2:16]([O:18][C:19](=[O:24])/[CH:20]=[C:21](/[O:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([F:14])[C:8]=1[F:7])\[CH3:22])[CH3:17]

참가 물질

5

반응물 3

HCID 808792,3-DifluorophenolHCID 2828353-Chloro-but-2-enoic acid ethyl ester2회HCID 23665647Potassium tert-butoxide

생성물 1

HCID 66895456(E)-3-(2,3-difluoro-phenoxy)-but-2-enoic acid ethyl ester수율 66.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
23 °C

실험 절차

Potassium t-butoxide (11.2 g, 0.100 mol) was added to a stirred solution of 2,3-difluoro-phenol (6.58 g, 0.051 mol) in tetrahydrofuran (30 mL) at 23° C. under nitrogen and the reaction mixture was heated to reflux for 0.75 h. The reaction mixture was cooled to 23° C. and a solution of 3-chloro-but-2-enoic acid ethyl ester (prepared as in Example 191 7.50 g, 0.050 mol) in tetrahydrofuran (40 mL) was added to the reaction mixture. The reaction mixture was refluxed for an additional 3 h. After this time, the mixture was concentrated in vacuo and the residue was diluted with water and extracted with diethyl ether. The organic layer was then washed with 5% aqueous sodium hydroxide solution followed by a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in vacuo to afford (E)-3-(2,3-difluoro-phenoxy)-but-2-enoic acid ethyl ester (8.01 g, 66%) as a yellow oil.

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 0.75 h
  3. temperatureThe reaction mixture was refluxed for an additional 3 h
  4. concentrationAfter this time, the mixture was concentrated in vacuo
  5. additionthe residue was diluted with water
  6. extractionextracted with diethyl ether
  7. washThe organic layer was then washed with 5% aqueous sodium hydroxide solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c3fda18a84d748aea71152ef19409e57
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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