Sodium Carbonate → 2-(2'-Chlorobiphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-phenyl}propanenitrile

HRID 2194890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194890
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]3[C:27]([Cl:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[Cl:30])=[CH:14][CH:13]=2)[C:9]#[N:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC.O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:28][C:27]1[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=1[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]3[C:27]([Cl:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[Cl:30])=[CH:14][CH:13]=2)[C:9]#[N:10])=[CH:4][CH:3]=1

Komponenten

6

Edukt 2

HCID 10340Sodium CarbonateHCID 674491012-(4-Bromophenyl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propanenitrile

Produkt 1

HCID 674482422-(2'-Chlorobiphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-phenyl}propanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11554889palladium acetate PPh3KatalysatorHCID 962WaterLösungsmittelHCID 67832237n-Propanol dioxaneLösungsmittel

Versuchsvorschrift

To a solution 2-(4-bromophenyl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propanenitrile (1 eq.) from step 1,2-chlorophenylboronic acid (2 eq.) in n-propanol:dioxane (1:2; 0.17M) at room temperature was added palladium acetate/triphenyl phosphine (1:3; 0.05 eq.) and aqueous Na2CO3 (2M; 4 eq.). The mixture was stiffed 30 min at 150° C. in microwave (Smith Creator; Personal Chemistry), cooled to room temperature, poured in water and extracted with EtOAc. The organic extract was washed with water, brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel, eluting with Hex/EtOAc 5% afforded the desired compound.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel
  8. washeluting with Hex/EtOAc 5%

Quellen und Nachweise

ORD-Eintrag
ord-42e34a5292b842d0833e41054358c434
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334308B2

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