Styrene → HCID 73991780, compound

HRID 1268289Notes

Reaction equation

[C:1]([O-:4])([O-])=O.[K+].[K+].[CH2:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Br[C:16]1[CH:17]=[C:18]([CH:21]=[C:22](Br)[CH:23]=1)[CH:19]=O>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CN(C=O)C.C(OCC)(=O)C.CC(O)=O.CC(O)=O.[Pd]>[CH:7]([C:16]1[CH:23]=[C:22]([CH:21]=[C:18]([CH:19]=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:17]=1)[CH:1]=[O:4])=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Bu4NBr (2.0 g, 6.3 mmol), K2CO3 (7.8 g, 56.7 mmol), Pd(Oac)2 (250 mg, 1.1 mmol) and styrene (20 mL, 175 mmol) were stirred for 5 min under nitrogen. To the mixture was added 3,5-dibromobenzaldehyde (5.0 g, 18.9 mmol) in dry DMF (5.0 mL), and the mixture was stirred at 65° C. for 16 h. The reaction mixture was diluted with ethyl acetate (20 mL) and the solution filtered. The filtrate was diluted with water and extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried over MgSO4, and concentrated under vacuum. To the residue was added a mixture of toluene/petroleum ether (1:1) (50 mL) and 3,5-distyryl-benzaldehyde (4.95 g, 85%) was isolated by filtration.

Workup

filtrationthe solution filtered
additionThe filtrate was diluted with water
extractionextracted with ethyl acetate (3×50 mL)
dry with materialdried over MgSO4
concentrationconcentrated under vacuum
additionTo the residue was added
additiona mixture of toluene/petroleum ether (1:1) (50 mL)

Sources & evidence

ORD record: ord-459fdc52e3384547a26b271fc846f41e
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06555577B1

Reaction notes

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