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

HRID 405193노트

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HRID 405193 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

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

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-68c8751463744f90910a9e1d1a9206fe
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748624B2

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