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ChemicalBook CAS DataBase List 1-BROMO-2-(4-BROMOPHENYL)ETHYLENE

1-BROMO-2-(4-BROMOPHENYL)ETHYLENE synthesis

4synthesis methods
136350-66-8 Synthesis
1-bromo-4-(2,2-dibromovinyl)benzene

136350-66-8
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Yield:778641-02-4 72%

Reaction Conditions:

with Ir(ppy)2(bpy);N-ethyl-N,N-diisopropylamine in 1,2-dichloro-ethane at 20; for 36 h;Inert atmosphere;Schlenk technique;Irradiation;Green chemistry;

Steps:

3. General Procedure for Synthesis of 2.

General procedure: An 25 mL oven-dried Schlenk tube was equipped with a stirring bar and Ir(ppy)2(bpy)PF6 (0.004mmol, 1 mol%). The Schlenk tube was degassed by using standard Schlenk techniques with an oil pump. Then 1,1-dibromoalkenes 1 (0.4mmol), iPr2NEt ( 1.2mmol, 3 eq.) and DCE (4 mL) were injected into the reaction tube. The reaction mixture was placed at a distance of about 5 cm from a blue LEDs and stirred at room temperature for 36h. The reaction mixture was diluted with DCM (30 mL) and 0.1 M HCL solution (2 x 20mL). The layers were separated. The aqueous layer was extracted with DCM (2 x 30 mL). The combined organic layers were washed with H2O (2 x 10 mL) and then were dried over Na2SO4. Afterwards, the organic solution was concentrated under reduced pressure using a rotary evaporator and purification was done by column chromatography on silica gel (200-300 mesh) with petroleum ether as the eluent to give the pure product 2.

References:

Sun, Wencheng;Teng, Qiaoling;Cheng, Dongping;Li, Xiaonian;Xu, Xiaoliang [Tetrahedron Letters,2020,vol. 61,# 3,art. no. 151410] Location in patent:supporting information