2,3-Difluorophenol → 2-(4-Chlorophenyl)-1-(3,4-difluoro-2-hydroxy-phenyl)-ethanone

HRID 14457

반응식

HRID 14457 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](Cl)=[O:14])=[CH:8][CH:7]=1.[F:16][C:17]1[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=1[OH:24]>ClCCCl.O>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([C:19]2[CH:20]=[CH:21][C:22]([F:23])=[C:17]([F:16])[C:18]=2[OH:24])=[O:14])=[CH:8][CH:7]=1

참가 물질

6

반응물 3

HCID 808792,3-DifluorophenolHCID 906924-Chlorophenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 686985132-(4-Chlorophenyl)-1-(3,4-difluoro-2-hydroxy-phenyl)-ethanone

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매2회HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

A mixture of aluminium chloride (7.66 g, 57.4 mmol, 1.5 eq.) and (4-chlorophenyl)acetyl chloride (8.7 g, 46 mmol, 1.2 eq.) in 1,2-dichloroethane (75 ml) is stirred at 0° C. for 30 min. A solution of 2,3-difluorophenol (5 g, 38.4 mmol) in 1,2-dichloroethane (25 ml) is added to the reaction mixture, which is heated in an oil bath at 90° C. overnight. The reaction mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic phase is dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo to afford a brown solid. This is triturated with hexane/ethyl acetate (9:1), filtered and dried to afford the title compound as a pale brown fine solid which is 87% pure by HPLC analysis.

후처리

  1. temperatureis heated in an oil bath at 90° C. overnight
  2. temperatureThe reaction mixture is cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. customto afford a brown solid
  8. customThis is triturated with hexane/ethyl acetate (9:1)
  9. filtrationfiltered
  10. customdried

출처 및 근거

ORD 기록
ord-9bbf5b40766140ed82fefb6b7021adb9
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732435B2

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