ChemicalBook CAS DataBase List 4-Cyano-4'-pentylbiphenyl

4-Cyano-4'-pentylbiphenyl synthesis

12synthesis methods

Product Name:4-Cyano-4'-pentylbiphenyl
CAS Number:40817-08-1
Molecular formula:C18H19N
Molecular Weight:249.35

63619-59-0 Synthesis

63619-59-0
132 suppliers
$6.00/250mg

40817-08-1
238 suppliers
$34.00/1g

Yield:40817-08-1 80%

Reaction Conditions:

Stage #1: 4-(4-pentylphenyl)bromobenzenewith iodine;magnesium in tetrahydrofuran at 70;
Stage #2: with N,N-dimethyl-formamide in tetrahydrofuran at 0; for 2 h;
Stage #3: with ammonia;iodine in tetrahydrofuran;water at 20; for 2 h;

Steps:

3.2 Typical experimental procedure for conversion of aromaticbromides into aromatic nitriles with Mg, DMF, I2, and aqNH3

General procedure: To a flask containing Mg turnings (0.29 g, 12 mmol) was added1-bromo-4-methylbenzene (1.37 g, 8.0 mmol) in THF (8 mL) at room temperature. After being stirred for 2 h, DMF (1.3 mL,12 mmol) was added to the reaction mixture. The obtained mixturewas stirred for 2 h at 0 ° C. Then, aq NH3 (7 mL, 28-30%) and I2 (4.06 g, 16 mmol) were added to the reaction mixture. After beingstirred for 2 h at room temperature, the reaction mixture waspoured into satd aq Na2SO3 solution and was extracted with CHCl3 (3*30 mL). The organic layer was dried over Na2SO4 and filtered.After removal of the solvent, the residue was purified by shortcolumn chromatography on silica gel (eluent: hexane/ethylacetate=9:1, v/v) to provide pure 4-methyl-1-benzonitrile (0.77 g) in 82% yield.

References:

Ishii, Genki;Harigae, Ryo;Moriyama, Katsuhiko;Togo, Hideo [Tetrahedron,2013,vol. 69,# 5,p. 1462 - 1469]

630-18-2 Synthesis