BENZONITRILE, 4-CYCLOHEXYL- synthesis

11synthesis methods

Product Name:BENZONITRILE, 4-CYCLOHEXYL-
CAS Number:27634-88-4
Molecular formula:C13H15N
Molecular Weight:185.26

108-85-0
337 suppliers
$5.00/10g

131379-14-1
24 suppliers
$191.00/50ml

27634-88-4
2 suppliers
inquiry

Yield:27634-88-4 90%

Reaction Conditions:

with N,N,N,N,-tetramethylethylenediamine;iron(III) chloride in tetrahydrofuran at 0; for 6 h;

Steps:

7.7-4

EXAMPLE 7; Entry No. 7-1 to Entry No. 7-6 Following the details given below, effects of various metallic reagents and halides on yield of the products were examined. A mixture of various aromatic zinc reagents shown by ArZnX (X = Br, I) (0.5 M THF solution, 4.0 mL, 2.0 mmol) and magnesium compounds shown by Me₃SiCH₂MgCl (1.1 M Et₂O solution 1.8 mL, 2.0 mmol) was charged in a dry reactor and stirred at 0°C for 0.5-1 hour. To the solution obtained, TMEDA (0.30 mL, 2.0 mmol), various halides (shown by "(FG)R_alkyl-X" in TABLE 6) (1.0 mmol) and then FeCl₃ (0.1 M THF solution, 0.5 mL, 0.05 mmol) were added at 0°C. The reaction mixture was stirred at 30°C for 6 hours. Saturated NH₄Cl aqueous solution was added to terminate the reaction. The mixture was filtered through a pad of Florisil (registered trademark) and concentrated in vacuum. The residue was purified by silica gel chromatography Entry No. 7-4 (4-Cyclohexylbenzonitrile) Halide: 3-bromocyclohexane (1.0 mmol) Aromatic zinc reagent: 4-cyanophenylzinc bromide (2.0 mmol) Reaction time: 6 hours Colorless oily substance (167 mg, 90%) FTIR (neat): cm^-1 2925 (s), 2852 (m), 2227 (m), 1607 (m), 1505 (m), 1449 (m), 1415 (w), 1177 (w), 1000 (w), 823 (s); ¹H NMR (500 MHz, CDCl₃): δ 7.56 (d, J = 8.6 Hz, 2H), 7.30 (d, J = 8.6 Hz, 2H), 2.12-2.00 (m, 1H), 1.92-1.80 (m, 4H), 1.80-1.69 (m, 1H), 1.47-1.33 (m, 4H), 1.33-1.20 (m, 1H); ¹³C NMR (125 MHz, CDCl₃): δ 153.4, 132.1 (2C), 127.6 (2C), 119.1, 109.5, 44.7, 33.9 (2C), 26.6 (2C), 25.9; Elemental analysis: Calcd. for C₁₃H₁₅N: C, 84.28; H, 8.16; N, 7.56. Found: C, 84.12; H, 8.36; N, 7.36.