Some common heterocyclic compound, 108-85-0, name is Bromocyclohexane, molecular formula is C6H11Br, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 108-85-0
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 0C for 0.5-1 hour. To the solution obtained, TMEDA (0.30 mL, 2.0 mmol), various halides (shown by “(FG)Ralkyl-X” in TABLE 6) (1.0 mmol) and then FeCl3 (0.1 M THF solution, 0.5 mL, 0.05 mmol) were added at 0C. The reaction mixture was stirred at 30C 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): delta 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): delta 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.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 108-85-0, its application will become more common.
Reference:
Patent; Japan Science and Technology Agency; EP1724248; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary