2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → Tert-butyl [4-(benzyloxy)-2-cyanophenyl]acetate

HRID 1474678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1474678
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](Br)=[C:13]([CH:16]=1)[C:14]#[N:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[C:19]([O:23][C:24](=[O:27])[CH2:25][Zn+])([CH3:22])([CH3:21])[CH3:20].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1COCC1.C(OCC)(=O)C.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]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:25][C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:27])=[C:13]([C:14]#[N:15])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 121019865-(Benzyloxy)-2-bromobenzonitrileHCID 178451183HCID 178451183, Verbindung

Produkt 1

HCID 86711182Tert-butyl [4-(benzyloxy)-2-cyanophenyl]acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 5-(benzyloxy)-2-bromobenzonitrile (0.73 g, 2.53 mmol) in THF (10 ml) was added 2-tert-butoxy-2-oxoethylzinc chloride (10.13 ml, 5.07 mmol). Nitrogen gas bubbled through the mixture for 10 min. then Pd2(dba)3 (0.116 g, 0.127 mmol) and X-PHOS (0.121 g, 0.253 mmol) were added and the resulting mixture heated at 60° C. for 50 min. The mixture was cooled, diluted with ethyl acetate (20 mL), washed with aqueous ammonium chloride (saturated, 1×15 mL), dried over MgSO4, filtered and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 50M, using a gradient eluant of EtOAc/Hexane (0-15%) to afford the title compound. LC/MS (m/z): 346 (M+H)+.

Aufarbeitung

  1. customNitrogen gas bubbled through the mixture for 10 min.
  2. temperatureThe mixture was cooled
  3. washwashed with aqueous ammonium chloride (saturated, 1×15 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel Biotage 50M

Quellen und Nachweise

ORD-Eintrag
ord-765c31d3cbd74762be142405258db4e0
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018224B2

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