2,4,6-Trimethyl-1,1'-biphenyl synthesis
- Product Name:2,4,6-Trimethyl-1,1'-biphenyl
- CAS Number:3976-35-0
- Molecular formula:C15H16
- Molecular Weight:196.2875
Yield:3976-35-0 90%
Reaction Conditions:
with Pd2Cl2(μ-Cl)2(PEt3)2;tetra(n-butyl)ammonium hydroxide in 1,4-dioxane at 100; for 4 h;Inert atmosphere;
Steps:
3.3. CeC cross coupling reaction between an arylhalide andorganobismuth compound
To a dioxane (3 ml) solution of 2-bromomesitylene (110 mg,0.55 mmol) and Ph3Bi (72.9 mg, 0.17 mmol) was addedpowdered K2CO3 (92.4 mg, 0.67 mmol) and [Pd2Cl2(m-Cl)2(PEt3)2](10 mg, 0.017 mmol). (A lower concentration of the catalystArX:Pd (35:1) also gave similar results). The whole was heated at100 C in an oil bath with stirring for 4 h. The contents werecooled to room temperature and acidified with dilute HCl(10 ml) and extracted with ethylacetate (15 ml 3). Thecombined extracts were washed with water (2 15 ml) andbrine (15 ml) and dried over anhydrous Na2SO4. This was filteredand dried under vacuum to give colorless oil (75 mg, 78% yield)and was characterized as Mes-Phenyl by 1H NMR spectroscopy.Similarly, other CeC coupling reactions were carried out andyields were calculated based on aryl groups of Ar3Bi consumedin the reactions.
References:
Chaudhari, Kamal R.;Wadawale, Amey P.;Jain, Vimal K. [Journal of Organometallic Chemistry,2012,vol. 698,p. 15 - 21] Location in patent:experimental part
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