Potassium Carbonate → (3-Bromophenyl)(3-(dibenzo[b,d]thiophen-2-yl)phenyl)diphenylsilane

HRID 403148Notes

Reaction equation

HRID 403148 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Si:8]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23](Br)[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.[CH:28]1[C:36]2[C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[S:33][C:32]=2[CH:31]=[CH:30][C:29]=1B(O)O.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:1][C:2]1[CH:3]=[C:4]([Si:8]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:38]3[CH:39]=[CH:40][C:34]4[S:33][C:32]5[CH:31]=[CH:30][CH:29]=[CH:28][C:36]=5[C:35]=4[CH:37]=3)[CH:22]=2)([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 297508Bis(3-bromophenyl)diphenylsilaneHCID 2794660Dibenzothiophene-2-boronic Acid

Product 1

HCID 86674051(3-Bromophenyl)(3-(dibenzo[b,d]thiophen-2-yl)phenyl)diphenylsilaneYield 60.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture solution of bis(3-bromophenyl)diphenylsilane (10.84 g, 21.92 mmol), dibenzo[b,d]thiophen-2-yl boronic acid (2.000 g, 8.77 mmol), Pd(PPh3)4 (0.101 g, 0.088 mmol) and K2CO3 (2.424 g, 17.54 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, v/v) as eluent to yield (3-bromophenyl)(3-(dibenzo[b,d]thiophen-2-yl)phenyl)diphenylsilane (3.16 g, 60% yield) as a white solid.

Workup

  1. customthe organic phase was isolated
  2. customevaporated to dryness
  3. customThe residue was purified by column chromatography on silica gel with hexane:DCM (9:1

Sources & evidence

ORD record
ord-9123af6d9eba42e98001d6dc196227ba
Source dataset
uspto-grants-2014_06
Patent number
US08748012B2

Reaction notes

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