Potassium Carbonate → HCID 86700954, compound

HRID 713595Notes

Reaction equation

HRID 713595 reaction equation
I[C:2]1[C:10]2[O:9][C:8]3[C:11]([Si:15]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:12][CH:13]=[CH:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=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>[Cl:34][C:35]1[CH:36]=[C:37]([C:2]2[C:10]3[O:9][C:8]4[C:11]([Si:15]([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)=[CH:12][CH:13]=[CH:14][C:7]=4[C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:38]=[CH:39][CH:40]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 86700955HCID 86700955, compound

Product 1

HCID 86700954HCID 86700954, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture solution of (6-Iododibenzo[b,d]furan-4-yl)triphenylsilane (6.60 g, 11.95 mmol), (3-chlorophenyl)boronic acid (2.80 g, 17.92 mmol), Pd(PPh3)4 (0.138 g, 0.119 mmol) and K2CO3 (3.30 g, 23.89 mmol) in toluene (100 mL) and water (15 mL) was refluxed under nitrogen for 24 hours. 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, v/v) as eluent to yield (6-(3-chlorophenyl)dibenzo[b,d]furan-4-yl)triphenylsilane (3.7 g, 58%) 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

Sources & evidence

ORD record
ord-44eca6eac66a48058d9f2a9105e9c490
Source dataset
uspto-grants-2015_11
Patent number
US09184399B2

Reaction notes

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