Hydrochloric Acid → HCID 57894173, 화합물

HRID 1822285노트

반응식

HRID 1822285 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]([CH3:20])[CH:17]=[C:16]([OH:21])[CH:15]=2)=[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.CCOCC>[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]([CH3:20])[CH:17]=[C:16]([O:21][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:15]=2)=[CH:9][C:8]=1[CH3:22])[CH3:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1442953-Bromo-4-fluorobenzotrifluorideHCID 578942263-[4-(3-Hydroxy-5-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester

생성물 1

HCID 57894173HCID 57894173, 화합물수율 71.3%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 3283Diethyl Ether용매

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온도
100 °C

실험 절차

A mixture of 3-[4-(3-hydroxy-5-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester (2.83 g, 9.01 mmol), 3-bromo-4-fluorobenzotrifluoride (2.19 g, 9.01 mmol) and 325 mesh potassium carbonate (1.49 g, 10.8 mmol) in dry DMSO (36 mL) is heated to 100° C. and stirred for 5 hours under N2. The reaction is cooled and acidified with 1 N HCl. The mixture is then diluted with Et2O and extracted with water. The organic layer is dried (Na2SO4), and the solvent 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 3.45 g (71%) of the title compound. Rf=0.54 (2/1 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 water
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. customthe solvent 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-ab5e88c545ab460694b82d00fcb4dbba
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608639B2

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