Styrene → HCID 68773456, compound

HRID 1176960Notes

Reaction equation

HRID 1176960 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)=[O:11])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Li+].[Cl-].[CH2:27]=[CH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[CH:27]([C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:9])[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH:10]=[CH:8][C:5]3[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=3)=[CH:14][CH:13]=2)=[O:11])=[CH:4][CH:3]=1)=[CH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

8

Reactant 4

HCID 7501StyreneHCID 11430Potassium CarbonateHCID 964304,4'-DibromobenzilHCID 433294Lithium Chloride

Product 1

HCID 68773456HCID 68773456, compoundYield 139.4%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A schlenk tube was charged with 4,4′-dibromobenzil (2.0 g, 5.4 mmol), K2CO3 (3.75 g, 27.2 mmol), Bu4NBr (1.75 g, 5.4 mmol), LiCl (0.23 g, 5.4 mmol), Pd(OAc)2 (0.12 g, 0.54 mmol), styrene (1.6 mL, 13.6 mmol), and 50 mL of dry DMF. The reaction mixture was heated at 100° C. for 14 h. The reaction mixture was allowed to cool down to room temperature and extracted with CH2Cl2. The organic phase was washed with H2O and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica gel, dichloromethane:hexanes=1:2 (v/v), then dichloromethane:hexanes=1:1 (v/v)) to give a light yellow solid (1.56 g, 69.3%). 1H NMR (300 MHz, CDCl3, δ): 7.97 (d, J=8.3 Hz, 4H), 7.62 (d, J=8.8 Hz, 4H), 7.53 (d, J=6.8 Hz, 4H), 7.27-7.40 (m, 6H), 7.26 (d, J=16.6 Hz, 2H), 7.12 (d, J=16.6 Hz, 2H). 13C{1H} NMR (75 MHz, CDCl3, δ): 193.82, 143.82, 136.45, 132.63, 131.83, 130.48, 128.83, 128.60, 127.17, 126.96, 126.84. HRMS-FAB (m/z): [M+H]+ calcd for C30H23O2, 415.1698; found, 415.1699. Anal. Calcd for C30H22O2: C, 86.93; H, 5.35. Found: C, 86.90; H, 5.26.

Workup

  1. temperatureto cool down to room temperature
  2. extractionextracted with CH2Cl2
  3. washThe organic phase was washed with H2O
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customThe crude product was purified by column chromatography (silica gel, dichloromethane

Sources & evidence

ORD record
ord-463615f471ca410790c112ac0ec531d8
Source dataset
uspto-grants-2010_11
Patent number
US07842830B2

Reaction notes

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