4-Iododibenzofuran → 4-Cyclohexyldibenzo[b,d]furan

HRID 929278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929278
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.I[C:10]1[C:15]2[O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:14]=2[CH:13]=[CH:12][CH:11]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[Cl-].[Cl-].[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1>[CH:1]1([C:22]2[C:17]3[O:16][C:15]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:18]=3[CH:19]=[CH:20][CH:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

7

Edukt 3

HCID 4582574-IododibenzofuranHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 178478990HCID 178478990, Verbindung

Produkt 1

HCID 1178939144-Cyclohexyldibenzo[b,d]furanAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

ZnCl2 (13.6 g, 100.0 mmol) and THF (600 mL) were cooled to 0° C. After that, cyclohexylmagnesium chloride (70.0 mL, 70.0 mmol, 1M in THF) was added at 0° C. The mixture was stirred for 15 min from 0° C. to room temperature. The mixture was bubbled with nitrogen for 15 min, followed by the addition of 4-iododibenzo[b,d]furan (11.8 g, 40.0 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (3.3 g, 8.0 mmol), and Pd2(dba)3 (1.8 g, 2.0 mmol). The resultant mixture was bubbled with nitrogen for 15 min and stirred for 48 h. The reaction mixture was quenched by the addition of saturated K2CO3 solution and extracted with DCM. The extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was purified by flash chromatography using 10% DCM/hexane to yield 4-cyclohexyldibenzo[b,d]furan (9.0 g, 90% yield) as a colorless oil.

Aufarbeitung

  1. customThe mixture was bubbled with nitrogen for 15 min
  2. customThe resultant mixture was bubbled with nitrogen for 15 min
  3. stirringstirred for 48 h
  4. customThe reaction mixture was quenched by the addition of saturated K2CO3 solution
  5. extractionextracted with DCM
  6. dry with materialThe extracts were dried over MgSO4
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9d3762a955ea4db1873138b3f8da8374
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09293712B2

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