Potassium Carbonate → HCID 86700954, compound

HRID 713597Notes

Reaction equation

HRID 713597 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 21%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of (6-iododibenzo[b,d]furan-4-yl)triphenylsilane (5.00 g, 9.05 mmol), (3-chlorophenyl) boronic acid (1.7 g, 11.3 mmol), Pd(PPh3)4 (0.105 g, 0.091 mmol) and K2CO3 (2.502 g, 18.10 mmol) in toluene (75 mL) and water (10 mL) was refluxed under nitrogen for 48 h. The organic layer was separated and the solvent was evaporated. The residue was purified by column chromatography on silica gel with hexane (EtOAc (95/5, v/v) as eluent followed by recrystallization from the same solvent to yield (6-(3-chlorophenyl)dibenzo[b,d]furan-4-yl)triphenylsilane (1.0 g, 21%) as a white solid.

Workup

  1. customThe organic layer was separated
  2. customthe solvent was evaporated
  3. customThe residue was purified by column chromatography on silica gel with hexane (EtOAc (95/5
  4. customv/v) as eluent followed by recrystallization from the same solvent

Sources & evidence

ORD record
ord-e11cd7bca8dc42169fe36488d10a299d
Source dataset
uspto-grants-2015_11
Patent number
US09184399B2

Reaction notes

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