Cesium fluoride → 2-(4'-Chloro-4-ethyl-2'-methylbiphen-3-yl)-4,4-dimethyl-cyclohexane-1,3-dione

HRID 400382

反応式

HRID 400382 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:18][CH3:19])=[C:6]([CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[CH2:11][CH2:10][C:9]2=[O:17])[CH:7]=1.[CH3:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1B(O)O.[F-].[Cs+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:27][C:25]1[CH:24]=[CH:23][C:22]([C:2]2[CH:3]=[CH:4][C:5]([CH2:18][CH3:19])=[C:6]([CH:8]3[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[CH2:11][CH2:10][C:9]3=[O:17])[CH:7]=2)=[C:21]([CH3:20])[CH:26]=1

参加物

6

反応物 3

HCID 25953Cesium fluorideHCID 5017600(4-Chloro-2-methylphenyl)boronic acidHCID 668701212-(5-Bromo-2-ethylphenyl)-4,4-dimethylcyclohexane-1,3-dione

生成物 1

HCID 1237151332-(4'-Chloro-4-ethyl-2'-methylbiphen-3-yl)-4,4-dimethyl-cyclohexane-1,3-dione

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2-(5-bromo-2-ethylphenyl)-4,4-dimethylcyclohexane-1,3-dione (0.194 g, 0.6 mmol), 2-methyl-4-chloro-phenylboronic acid (0.153 g, 0.9 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (complex with dichloromethane 1:1) (80 mg, 0.098 mmol) and cesium fluoride (0.608 g, 4 mmol) are stirred together in 1,2-dimethoxyethane (4 ml) and the reaction mixture is heated at 80° C. overnight. The warm reaction mixture is filtered, washing the filter cake with 9:1 dichloromethane:methanol. The mixture is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel to give 2-(4′-chloro-4-ethyl-2′-methylbiphen-3-yl)-4,4-dimethyl-cyclohexane-1,3-dione.

後処理

  1. customThe warm reaction mixture
  2. filtrationis filtered
  3. washwashing the filter cake with 9:1 dichloromethane
  4. concentrationThe mixture is concentrated under reduced pressure
  5. customthe residue is purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-2b6c5141eef649918800f0a6fff9105f
出典データセット
uspto-grants-2014_06
特許番号
US08741806B2

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