Potassium Carbonate → (5-Bromo-3'-(dibenzo[b,d]furan-4-yl)[1,1'-biphenyl]-3-yl)triphenylsilane

HRID 713590Notes

Reaction equation

HRID 713590 reaction equation
Br[C:2]1[CH:3]=[C:4]([Si:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:6]([Br:8])[CH:7]=1.C1[C:36]2[C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[O:33][C:32]=2[C:31](C2C=C(B3OC(C)(C)C(C)(C)O3)C=CC=2)=CC=1.C([O-])([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:8][C:6]1[CH:5]=[C:4]([Si:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]=[C:2]([C:7]2[CH:2]=[CH:3][CH:4]=[C:36]([C:35]3[C:34]4[O:33][C:32]5[CH:12]=[CH:11][CH:10]=[CH:15][C:31]=5[C:40]=4[CH:39]=[CH:38][CH:37]=3)[CH:6]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 575885922-(3-(Dibenzo[b,d]furan-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 58926930HCID 58926930, compound

Product 1

HCID 86700951(5-Bromo-3'-(dibenzo[b,d]furan-4-yl)[1,1'-biphenyl]-3-yl)triphenylsilaneYield 45.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of (3,5-Dibromophenyl)triphenylsilane (4.27 g, 8.64 mmol), 2-(3-(dibenzo[b,d]furan-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.6 g, 4.32 mmol), Pd(PPh3)4 (0.100 g, 0.086 mmol) and K2CO3 (1.792 g, 12.96 mmol) in toluene (100 mL) and water (10 mL) was refluxed under nitrogen overnight. After cooling to room temperature, the organic phase was isolated, and the solvent was evaporated. The residue was purified by column chromatography on silica gel with hexane/DCM (4/1 to 3/1, v/v) as eluent to yield (5-Bromo-3′-(dibenzo[b,d]furan-4-yl)[1,1′-biphenyl]-3-yl)triphenylsilane (1.3 g, 45%) as a white solid.

Workup

  1. customthe organic phase was isolated
  2. customthe solvent was evaporated
  3. customThe residue was purified by column chromatography on silica gel with hexane/DCM (4/1 to 3/1

Sources & evidence

ORD record
ord-55d9814bab71498bac825b61adfd2d20
Source dataset
uspto-grants-2015_11
Patent number
US09184399B2

Reaction notes

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