Cesium carbonate → 3-{4-[3-(4-Chloro-2-phenoxy-phenoxy)-phenoxy]-2-methyl-phenyl}-propionic acid methyl ester

HRID 1822257

반응식

HRID 1822257 반응식
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=2)=[CH:8][C:7]=1[CH3:20].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C>CN1CCCC1=O.[Cu]Cl>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:29][C:26]3[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][C:25]=3[O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:14]=2)=[CH:8][C:7]=1[CH3:20]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 127742954-Chloro-2-phenoxyphenolHCID 578941923-[4-(3-Bromo-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester

생성물 1

HCID 578942213-{4-[3-(4-Chloro-2-phenoxy-phenoxy)-phenoxy]-2-methyl-phenyl}-propionic acid methyl ester수율 33.2%

시약·촉매·용매 2

HCID 62652Cuprous chloride촉매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

A mixture of 3-[4-(3-bromo-phenoxy)-2-methyl-phenyl]-propionic acid methyl ester (0.474 g, 1.36 mmol), 4-chloro-2-phenoxy-phenol (0.30 g, 1.36 mmol), cesium carbonate (0.531 g, 1.63 mmol), copper (I) chloride (0.067 g, 0.677 mmol) and 2,2,6,6-tetramethyl-3,5-heptanedione (0.063 g, 0.342 mmol) in 1-methyl-2-pyrrolidinone (5 mL) is heated to 120° C. for 20 hours under N2. The reaction is cooled and quenched with 1 N HCl (20 mL). The mixture is then diluted with Et2O and extracted with water. 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 0.221 g (33%) of the title compound. Rf=0.29 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C29H25O5Cl 488, found 489 and 351 (M+1 and M+3, 100%).

후처리

  1. temperatureThe reaction is cooled
  2. customquenched with 1 N HCl (20 mL)
  3. additionThe mixture is then diluted with Et2O
  4. extractionextracted with water
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. customthe solvent is removed in vacuo
  7. customto afford crude product that
  8. customis absorbed on silica gel
  9. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-4bf89494741449f5a7848209732cd3dc
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608639B2

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