Styrene → HCID 73990325, compound

HRID 2416407Notes

Reaction equation

HRID 2416407 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Si:8]([C:23]2[CH:28]=[CH:27][C:26](Br)=[CH:25][CH:24]=2)([C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH2:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC([O-])=O.CC([O-])=O.[Pd+2].CC(N(C)C)=O>[C:6]1([CH:30]=[CH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=1[Si:8]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:30]=[CH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 3

HCID 7501StyreneHCID 11430Potassium CarbonateHCID 12729346Tetrakis(4-bromophenyl)silane

Product 1

HCID 73990325HCID 73990325, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A round bottom flask (50 mL) equipped with a teflon coated stir bar was charged with tetrakis(4-bromophenyl)silane (326 mg, 0.5 mmol), styrene (2.0 g, 12 mmol), Pd(OAc)2 (14 mg, 12 mol %), K2CO3 (690 mg, 5 mmol), n-Bu4NBr (645 mg, 2 mmol), and DMA (10 mL). The flask was fitted with a rubber septum and purged with nitrogen prior to heating (80° C.) with stirring for 48 hours. The reaction mixture was allowed to cool to room temperature, diluted with CH2Cl2, and washed five times with brine. The organic phase was dried with MgSO4, filtered through silica gel and the solvent was evaporated under reduced pressure. The residue was dissolved in CHCl3 and precipitated with hexanes. The colorless needle-like crystals were collected (52% yield). 1H NMR (CDCl3): δ 7.61 (d, J=8.0 Hz, 8H), 7.55 (m, 16H), 7.38 (t, J=7.3 Hz, J=8.0 Hz, 8H), 7.29 (t, J=7.3 Hz, 4H), 7.17 (AA′BB′ pattern, J=16.4 Hz, 8H). 13C NMR (CDCl3) δ 138.5, 137.1, 136.7, 133.4, 129.5, 128.6, 128.4, 127.7,126.5, 125.9.

Workup

  1. customA round bottom flask (50 mL) equipped with a teflon coated stir bar
  2. customThe flask was fitted with a rubber septum
  3. custompurged with nitrogen
  4. temperatureto cool to room temperature
  5. additiondiluted with CH2Cl2
  6. washwashed five times with brine
  7. dry with materialThe organic phase was dried with MgSO4
  8. filtrationfiltered through silica gel
  9. customthe solvent was evaporated under reduced pressure
  10. dissolutionThe residue was dissolved in CHCl3
  11. customprecipitated with hexanes
  12. customThe colorless needle-like crystals were collected (52% yield)

Sources & evidence

ORD record
ord-7c03add6e97b46ae8a799d029dcc5bea
Source dataset
uspto-grants-2004_11
Patent number
US06824890B2

Reaction notes

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