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

HRID 512578

反応式

HRID 512578 の反応式
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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 2734996copper(II) trifluoromethanesulfonate触媒HCID 313Hydrochloric Acid溶媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
160 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-570eafc324334c1e89548e3de89fb7da
出典データセット
uspto-grants-2015_08
特許番号
US09102642B2

関連ノート

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