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ChemicalBook CAS DataBase List α-Bromocinnamaldehyde
5443-49-2

α-Bromocinnamaldehyde synthesis

3synthesis methods
The synthesis of α-Bromocinnamaldehyde is as follows:
The cinnamaldehyde and glacial acetic acid were stirred and bromine was added after cooling. Then add anhydrous potassium carbonate, reactants heated reflux for half an hour, cooling, precipitation coarse product. The crude product is dissolved by ethanol and recrystallized to obtain the finished product with a yield of about 80%.
-

Yield:5443-49-2 85%

Reaction Conditions:

with propane 3-bromo-1-(triphenylphosphonium) tribromide in dichloromethane at 20; for 4 h;

Steps:

3.3. General experimental procedure for bromination of alkenes

General procedure: In a typical reaction, the alkene (3 mmol) was dissolved indichloromethane (5 mL) and stirred well for 2 min. Propane 3-bromo-1-(triphenyl phosphonium) tribromide II (3 mmol) dissolvedin dichloromethane (5 mL) andwas added to alkene solutiondropwise with constant stirring at room temperature. The progressof the reaction was monitored by TLC and GC. After completion ofthe reaction and disappearance of the yellow-orange color of reagentII, the solvent evaporated and diethyl ether was added(3 5 ml). The mixture was filtered and the solvent evaporated. The crude product thus obtained and then subjected to a shortcolumn of silica gel using a mixture of n-hexane and ethyl acetate(8:2) as the eluent. All of the isolated products are known andphysical data have been reported in the literature. The mainproducts, reaction times and isolated yields are tabulated in Table 2.To confirm, the products were subjected to DSC and GC/MS andspectra were compared and validated with the NIST library (seesupporting information).

References:

Nokhbeh, Seyed Reza;Gholizadeh, Mostafa;Salimi, Alireza;Sparkes, Hazel A. [Journal of Molecular Structure,2019,vol. 1195,p. 542 - 554]

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