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Potassium Carbonate → (4-Bromophenyl)(4-(dibenzo[b,d]thiophen-4-yl)phenyl)diphenylsilane

HRID 403152
Notes
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Reaction equation

HRID 403152 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:18]1[CH:23]=[CH:22][C:21]([Si:24]([C:37]2[CH:42]=[CH:41][C:40]([Br:43])=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:20][CH:19]=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:43][C:40]1[CH:39]=[CH:38][C:37]([Si:24]([C:31]2[CH:32]=[CH:33][C:34]([C:4]3[C:5]4[S:6][C:7]5[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=5[C:9]=4[CH:1]=[CH:2][CH:3]=3)=[CH:35][CH:36]=2)([C:21]2[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:42][CH:41]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 297512Bis(4-bromophenyl)diphenylsilaneHCID 2734329Dibenzothiophene-4-boronic acid

Product 1

HCID 86674054(4-Bromophenyl)(4-(dibenzo[b,d]thiophen-4-yl)phenyl)diphenylsilaneYield 79.4%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent

Procedure

A mixture solution of dibenzo[b,d]thiophen-4-ylboronic acid (2.5 g, 10.96 mmol), bis(4-bromophenyl)diphenylsilane (11.92 g, 24.11 mmol), Pd(PPh3)4 (0.253 g, 0.219 mmol), and K2CO3 (9.09 g, 65.8 mmol) in toluene (90 mL) and water (30 mL) was stirred at 90° C. under nitrogen overnight. After cooling to room temperature, the organic phase was isolated, and the aqueous phase was extracted with toluene. The combined organic solution was dried over Na2SO4. Upon evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane:DCM(9/1, v/v) as eluent to yield (4-bromophenyl)(4-(dibenzo[b,d]thiophen-4-yl)phenyl)diphenylsilane (5.2 g, 79%) as a white powder.

Workup

  1. customthe organic phase was isolated
  2. extractionthe aqueous phase was extracted with toluene
  3. dry with materialThe combined organic solution was dried over Na2SO4
  4. customUpon evaporation of the solvent
  5. customthe residue was purified by column chromatography on silica gel with hexane

Sources & evidence

ORD record
ord-d7399047acc44b19aae05a3da573ec3c
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748012B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes