Potassium Carbonate → HCID 59655978, compound

HRID 1782669Notes

Reaction equation

HRID 1782669 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:18]1[CH:23]=[CH:22][C:21]([Si:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.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>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([C:18]2[CH:23]=[CH:22][C:21]([Si:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=2)=[CH:3][CH:2]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 138897Silane, (4-bromophenyl)trimethyl-HCID 2734328Dibenzofuran-4-boronic acid

Product 1

HCID 59655978HCID 59655978, compoundYield 96.8%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of dibenzofuran-4-yl-boronic acid (20.0 g, 94.3 mmol), (4-bromo-phenyl)-trimethyl-silane (21.62 g, 94.3 mmol), K2CO3 (39.1 g, 3 equiv., 283 mmol) in toluene (100 mL), ethanol (60 mL) and water (30 mL) was purged with nitrogen for 5 min (bubbled into solution) and treated with Pd(PPh3)4 (3.59 g, 2.9 mmol). After heating to 80° C. for 4 h, the solution was cooled to room temperature, poured into water (300 mL) and extracted with ethyl acetate (300 mL). The organic phase was washed with sat'd aq NaCl, dried over anhydrous MgSO4 , filtered and concentrated in vacuo. Purification by flash column chromatography (5-20% ethyl acetate in heptane) afforded (4-dibenzofuran-4-yl-phenyl)-trimethyl-silane as a colorless oil (28.9 g, 96%).

Workup

  1. custom(bubbled into solution)
  2. temperaturethe solution was cooled to room temperature
  3. extractionextracted with ethyl acetate (300 mL)
  4. washThe organic phase was washed with sat'd aq NaCl
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash column chromatography (5-20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-101023113fe040809a5c82f0e36ff349
Source dataset
uspto-grants-2009_03
Patent number
US07498356B2

Reaction notes

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