Potassium Carbonate → HCID 86700956, compound

HRID 713596Notes

Reaction equation

HRID 713596 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.CC1(C)C(C)(C)OB([C:36]2[CH:53]=[CH:52][C:51]3[C:50]4[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=4)[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[C:38]=3[CH:37]=2)O1.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: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:3]=[C:2]([C:47]2[CH:48]=[CH:49][C:50]3[C:51]4[C:38](=[CH:37][CH:36]=[CH:53][CH:52]=4)[C:39]4[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:45]=3[CH:46]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 587694494,4,5,5-Tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolaneHCID 58926930HCID 58926930, compound

Product 1

HCID 86700956HCID 86700956, compoundYield 52.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of (3,5-dibromophenyl)triphenylsilane (2.20 g, 4.45 mmol), 4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane (3.15 g, 8.90 mmol), Pd(PPh3)4 (0.051 g, 0.045 mmol) and K2CO3 (1.23 g, 8.90 mmol) in toluene (100 mL) and water (20 mL) was refluxed under nitrogen overnight. After cooling to room temperature, the organic phase was isolated, filtered through a short plug of Celite® and the solvent was evaporated. The residue was purified by column chromatography on silica gel with hexane/DCM (7/3, v/v) as eluent followed by recrystallization from the same solvent to yield (3-bromo-5-(triphenylen-2-yl)phenyl)triphenylsilane (1.50 g, 52%) as a white solid.

Workup

  1. customthe organic phase was isolated
  2. filtrationfiltered through a short plug of Celite®
  3. customthe solvent was evaporated
  4. customThe residue was purified by column chromatography on silica gel with hexane/DCM (7/3
  5. customv/v) as eluent followed by recrystallization from the same solvent

Sources & evidence

ORD record
ord-e9e0938aae9d44228fba1aa43b3c4f17
Source dataset
uspto-grants-2015_11
Patent number
US09184399B2

Reaction notes

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