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Styrene → HCID 73990325, 화합물

HRID 2416407
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HRID 2416407 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

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

생성물 1

HCID 73990325HCID 73990325, 화합물수율 52%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매
HCID 167845
palladium(II) acetate
촉매
HCID 31374Dimethylacetamide용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7c03add6e97b46ae8a799d029dcc5bea
출처 데이터셋
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06824890B2

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