1,1'-BIPHENYL, 3-(CHLOROMETHYL)- synthesis
- Product Name:1,1'-BIPHENYL, 3-(CHLOROMETHYL)-
- CAS Number:38580-82-4
- Molecular formula:C13H11Cl
- Molecular Weight:202.68
Yield:38580-82-4 95%
Reaction Conditions:
with palladium diacetate;caesium carbonate;tricyclohexylphosphine tetrafluoroborate in water;toluene at 80; for 2 h;Schlenk technique;Inert atmosphere;Suzuki-Miyaura Coupling;
Steps:
3.1. General Procedure for the Selective Coupling Reaction of o-(or m-, or p-)chloromethyl Bromobenzene with Arylboronic Acid
General procedure: A Schlenk tube (20 mL) was charged with o-(or m-, or p-)chloromethyl bromobenzene (0.3 mmol),arylboronic acid (0.33 mmol), Pd(OAc)2 (0.2 mol %), PCy3·HBF4 (0.4 mol %), and Cs2CO3 (2 equiv.).The tube was degassed for 30 s and then was filled with argon. This operation was repeated threetimes. After toluene (1.0 mL) and H2O (0.1 mL) were added under argon atmosphere, the resultingreaction mixture was stirred at 80 °C for 2 h under argon. After the completion of the reaction, thereaction mixture was allowed to cool to room temperature. The solution was quenched with water(10 mL) and extracted with EtOAc (3 × 10 mL). The combined EtOAc extracts were dried overanhydrous Na2SO4 and filtered, followed by solvent removal under reduced pressure. The residuewas purified by flash column chromatography on silica gel using petroleum ether/EtOAc as theeluent.
References:
Pei, Ming-ming;Liu, Ping;Liu, Yan;Lv, Xin-ming;Ma, Xiao-wei;Dai, Bin [Molecules,2018,vol. 23,# 2,art. no. 433]
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