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

HRID 713592Notes

Reaction equation

HRID 713592 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]([C:14]2[CH:15]=[C:16](B3OC(C)(C)C(C)(C)O3)[CH:17]=[CH:18][CH:19]=2)=[CH:3][CH:2]=1.[Br:29][C:30]1[CH:31]=[C:32]([Si:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:33]=[C:34](Br)[CH:35]=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:29][C:30]1[CH:31]=[C:32]([Si:37]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:33]=[C:34]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([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:15]=2)[CH:35]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 58926930HCID 58926930, compoundHCID 595753552-(3-(Dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 86700953(5-Bromo-3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)triphenylsilaneYield 80.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.00 g, 5.18 mmol), (3,5-dibromophenyl)triphenylsilane (5.12 g, 10.35 mmol), Pd(PPh3)4 (0.120 g, 0.104 mmol), K2CO3 (2.147 g, 15.53 mmol) in toluene (100 mL) and water (20 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 (2/1 v/v) as eluent to yield (5-bromo-3′-(dibenzo[b,d]thiophen-4-yl)-[1,1′-biphenyl]-3-yl)triphenylsilane (2.8 g, 80% yield) 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 (2/1 v/v) as eluent

Sources & evidence

ORD record
ord-f5e803d40d754a029eb02fcc6dd6dc4f
Source dataset
uspto-grants-2015_11
Patent number
US09184399B2

Reaction notes

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