Cesium carbonate → 4-[4-(4-Chloro-3-fluorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione

HRID 512578노트

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HRID 512578 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]2=[O:19])=[C:4]([CH2:20][CH3:21])[CH:3]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][C:24]=1[F:30].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.ClCCl.Cl.FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:2]2[CH:7]=[CH:6][C:5]([CH:8]3[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]3=[O:19])=[C:4]([CH2:20][CH3:21])[CH:3]=2)=[CH:25][C:24]=1[F:30]

참가 물질

8

반응물 3

HCID 10796Cesium carbonateHCID 27245234-Chloro-3-fluorophenolHCID 497653874-(4-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

생성물 1

HCID 666777344-[4-(4-Chloro-3-fluorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione

시약·촉매·용매 4

HCID 2734996copper(II) trifluoromethanesulfonate촉매HCID 313Hydrochloric Acid용매HCID 1140Toluene용매HCID 6344Dichloromethane용매

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온도
160 °C

실험 절차

A mixture of 4-(4-bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione (0.20 g, 0.57 mmol), 4-chloro-3-fluorophenol (0.41 g, 2.83 mmol), cesium carbonate (0.40 g, 1.13 mmol), copper(II) trifluoromethanesulfonate (0.01 g, 0.03 mmol) and powdered molecular sieve, 4 Å (0.40 g) in dry toluene (3.5 ml) is heated to 160° C. under microwave irradiation for 1 hour. The mixture is cooled to room temperature diluted with dichloromethane and 2M aqueous hydrochloric acid (10 ml) and passed through a phase separation cartridge. The organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is dissolved in N,N-dimethylformamide (1 ml) and purified by preparative reverse phase HPLC to give 4-[4-(4-chloro-3-fluorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione.

후처리

  1. temperatureThe mixture is cooled to room temperature
  2. custompassed through a phase separation cartridge
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate is evaporated under reduced pressure
  6. dissolutionThe residue is dissolved in N,N-dimethylformamide (1 ml)
  7. custompurified by preparative reverse phase HPLC

출처 및 근거

ORD 기록
ord-570eafc324334c1e89548e3de89fb7da
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102642B2

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