Hydrochloric Acid → 3-{4-[5-(2-Bromo-4-trifluoromethyl-phenoxy)-2-methyl-phenoxy]-2-methyl-phenyl}-propionic acid ethyl ester

HRID 1822323노트

반응식

HRID 1822323 반응식
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:15]=2[CH3:21])=[CH:9][C:8]=1[CH3:22])[CH3:2].[Br:24][C:25]1[CH:26]=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:28]=[CH:29][C:30]=1F.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.O>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20][C:30]3[CH:29]=[CH:28][C:27]([C:32]([F:35])([F:34])[F:33])=[CH:26][C:25]=3[Br:24])[CH:17]=[CH:16][C:15]=2[CH3:21])=[CH:9][C:8]=1[CH3:22])[CH3:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1442953-Bromo-4-fluorobenzotrifluorideHCID 578941473-[4-(5-Hydroxy-2-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester

생성물 1

HCID 578942203-{4-[5-(2-Bromo-4-trifluoromethyl-phenoxy)-2-methyl-phenoxy]-2-methyl-phenyl}-propionic acid ethyl ester수율 81.2%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A mixture of 3-[4-(5-hydroxy-2-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester (Example 84, Step D) (0.46 g, 1.46 mmol), 3-bromo-4-fluorobenzotrifluoride (0.35 g, 1.45 mmol) and 325 mesh potassium carbonate (0.21 g, 1.52 mmol) in dry DMSO (10 mL) is heated to 100° C. and stirred for 6 hours under N2. The reaction is cooled and acidified with 1 N HCl. The mixture is diluted with water and extracted with Et2O. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 9/1 hexanes/ethyl acetate to afford 0.633 g (81%) of the title compound. Rf=0.38 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C26H24O4F3Br 536, found 554 and 556 (M+NH4, 100%).

후처리

  1. temperatureThe reaction is cooled
  2. extractionextracted with Et2O
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. customthe solvent is removed in vacuo
  5. customto afford crude product that
  6. customis absorbed on silica gel
  7. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-01cb5e49d1274020996549a67481f4e6
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608639B2

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