Potassium Carbonate → 4'-Chloro-2-methyl-[1,1'-biphenyl]-4-amine

HRID 405193ノート

反応式

HRID 405193 の反応式
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[CH3:9].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[CH3:9])=[CH:13][CH:12]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 233594-Bromo-3-methylanilineHCID 742994-Chlorophenylboronic acid

生成物 1

HCID 600391884'-Chloro-2-methyl-[1,1'-biphenyl]-4-amine

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

4-bromo-3-methylaniline (5.1 g, 27.4 mmol), 4-chlorophenylboronic acid (5.1 g, 32.9 mmol), Pd(dppf)Cl2 (1.1 g, 1.4 mmol), and 2M aqueous K2CO3 (27.4 mL, 54.8 mmol) were dissolved in 1,4-dioxane (110 mL) and the resulting mixture was heated to 100° C. After 2 h the resulting mixture was cooled to room temperature, concentrated, diluted with EtOAc and 4M aqueous NaCl, and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organics were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

後処理

  1. temperatureAfter 2 h the resulting mixture was cooled to room temperature
  2. concentrationconcentrated
  3. additiondiluted with EtOAc and 4M aqueous NaCl
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with EtOAc
  6. dry with materialthe combined organics were dried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified via column chromatography

出典と根拠

ORDレコード
ord-68c8751463744f90910a9e1d1a9206fe
出典データセット
uspto-grants-2014_06
特許番号
US08748624B2

反応ノート

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