Synthetic Route of 6621-59-6,Some common heterocyclic compound, 6621-59-6, name is 6-Bromohexanenitrile, molecular formula is C6H10BrN, 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.
A mixture of 2 (200mg, 0.34mmol), 6-bromohexanenitrile (180mg, 1.0mmol) and powdered NaH (95%; 17mg, 0.67mmol) in dry DMF (2.0mL) was stirred at room temperature under nitrogen for 2.5h. Saturated Na2CO3 buffer (6mL) was added, and the mixture extracted with ethyl acetate (25mL). The organic layer was washed with buffer (4×5mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using cyclohexane: ethyl acetate (1:1) containing 1% Et3N to give 133mg (57%) of 6 as a white foam: 1H NMR (CDCl3): delta 7.83 (d, J=7.2Hz, 2H, H-2?, H-6?), 7.38 (d, J=7.8Hz, 2H, H-3?, H-5?), 6.69 (d, J=8.1Hz, 1H, H-1), 6.54 (d, J=8.1Hz, 1H, H-2), 4.35 (s, 1H, H-5), 4.05-3.85 (m, 1H, H-1?), 3.80-3.57 (m, 1H, H-1?), 3.05 (d, J=6.3Hz, 1H, H-9), 3.03 (d, J=12Hz, 1H, H-10), 2.98-2.79 (m, 1H, H-8), 2.69 (dd, J=11.7Hz, J=4.8Hz, 1H, H-16), 2.52 (s, 3H, H-7?), 2.40 (t, J=7.2Hz, 2H, H-5?), 2.32-2.17 (m, 4H, H-10, H-16, H-22), 2.15-2.00 (m, 1H, H-15), 1.98-1.50 (m, 9H, H-7, H-15, H-18, H-2?, H-4?), 1.43 (s, 3H, H-21), 1.33-1.28 (m, 2H, H-3?), 1.23 (s, 3H, H-20), 1.18-1.00 (m, 2H, H-8, H-17), 0.93-0.79 (m, 1H, H-23), 0.78-0.62 (m, 1H, H-17), 0.61-0.46 (m, 2H, H-24, H-25), 0.2-0.07 (m, 2H, H-24, H-25); HRMS m/z calcd for [M+H]+ 661.3306, found 661.3328; Anal. Calcd for C38H48N2O6S: C, 69.06; H, 7.32; N, 4.24; found: C, 69.32; H, 7.20; N, 4.34.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromohexanenitrile, its application will become more common.
Reference:
Article; Srivastava, Shefali; Fergason-Cantrell, Emily A.; Nahas, Roger I.; Lever, John R.; Tetrahedron; vol. 72; 40; (2016); p. 6127 – 6135;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts