3,3'-Bis(trifluoroMethyl)-1,1'-biphenyl synthesis
- Product Name:3,3'-Bis(trifluoroMethyl)-1,1'-biphenyl
- CAS Number:580-82-5
- Molecular formula:C14H8F6
- Molecular Weight:290.2
199465-55-9
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580-82-5
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Yield:580-82-5 653 mg
Reaction Conditions:
with p-benzoquinone;cobalt(II) bromide in acetonitrile at 20;
Steps:
Oxidative Synthesis of Symmetrical Biaryl Using p-Benzoquinone as Oxidant; General Procedure
General procedure: Oxidative Synthesis of Symmetrical Biaryl Using p-Benzoquinone as Oxidant; General Procedure To a solution of CoBr2 (220 mg, 1 mmol, 13 mol%) and zinc powder(1.3 g, 20 mmol) in MeCN (5 mL) were successively added at r.t. allylchloride (250 μL, 3 mmol) and TFA (50 μL), causing an immediate risein temperature and color change to dark grey. After stirring the re-sulting mixture for 3 min, aryl bromide (7.5 mmol) was added. Themedium was then stirred at r.t. until the aryl halide was consumed.The amount of the corresponding organozinc species was measuredby reaction with I2 and GC analysis using an internal reference (do-decane 100 μL). When the aromatic halide had been consumed, p-benzoquinone (405 mg, 3.75 mmol) was added and the mixture wasstirred overnight. The mixture was hydrolyzed by 2 M HCl and ex-tracted with Et2O. The organic layer was dried (MgSO4). Evaporationof solvent and purification by column chromatography (silica gel, pe-troleum ether/Et2O) afforded the symmetrical biaryl characterized byNMR (1H, 13C).
References:
Bourne-Branchu, Yann;Moncomble, Aurélien;Corpet, Martin;Danoun, Gregory;Gosmini, Corinne [Synthesis,2016,vol. 48,# 19,art. no. SS-2016-C0348-OP,p. 3352 - 3356]
401-78-5
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401-81-0
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1423-26-3
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580-82-5
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131086-40-3
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