Potassium Carbonate → (3-Bromophenyl)(3'-(dibenzo [b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)diphenylsilane

HRID 403147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403147
Br[C:2]1[CH:3]=[C:4]([Si:8]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:28]1[C:36]23[CH:37]=[CH:38][CH:39]=[CH:40][C:35]2=CO[C:32]3=[C:31]([C:41]2[CH:42]=[C:43](B3OC(C)(C)C(C)(C)O3)[CH:44]=[CH:45][CH:46]=2)[CH:30]=[CH:29]1.[C:56]([O-:59])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:27][C:23]1[CH:22]=[C:21]([Si:8]([C:4]2[CH:3]=[C:2]([C:45]3[CH:44]=[CH:43][CH:42]=[C:41]([C:31]4[C:32]5[O:59][C:56]6[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=6[C:36]=5[CH:28]=[CH:29][CH:30]=4)[CH:46]=3)[CH:7]=[CH:6][CH:5]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:26]=[CH:25][CH:24]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 297508Bis(3-bromophenyl)diphenylsilaneHCID 710601992-(3-(Dibenzo[b,c]furan-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 86674050(3-Bromophenyl)(3'-(dibenzo [b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)diphenylsilaneAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture solution of bis(3-bromophenyl)diphenylsilane (8.01 g, 16.21 mmol), 2-(3-(dibenzo[b,c]furan-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.00 g, 8.10 mmol), K2CO3 (2.240 g, 16.21 mmol), Pd(PPh3)4 (0.15 g, 0.162 mmol) in toluene (200 mL) and water (50 mL) was refluxed under nitrogen overnight. After cooling to room temperature, the organic phase was isolated and evaporated to dryness. The residue was purified by column chromatography on silica gel with hexane:DCM (9/1 to 3/1, v/v) as eluent to yield (3-bromophenyl)(3′-(dibenzo [b,d]furan-4-yl)-[1,1′-biphenyl]-3-yl)diphenylsilane (3.2 g, 60%) as a white solid.

Aufarbeitung

  1. customthe organic phase was isolated
  2. customevaporated to dryness
  3. customThe residue was purified by column chromatography on silica gel with hexane

Quellen und Nachweise

ORD-Eintrag
ord-d1db6c353a234c9f8281d8ec6c97ece1
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748012B2

Notizen zur Reaktion

Wird geladen…