Electric Literature of 16799-05-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 16799-05-6, name is 3-Chlorophenethyl Bromide belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
Example 57; (3R)-1-[2-(3-Chlorophenyl)ethyl]-3-{[2-piperidin-1-yl-2-(2-thienyl)propanoyl]oxy}-1-azoniabicyclo[2.2.2]octane bromide (Isomer 1); (3R)-1-Azabicyclo[2.2.2]oct-3-yl 2-piperidin-1-yl-2-(2-thienyl)propanoate (Example 57b, Isomer 1, 0.5 g) in acetonitrile (3 mL) was treated with 1-(2-bromoethyl)-3-chlorobenzene (0.35 g) and the mixture stirred and heated at 80 C. for 4 h. The mixture was concentrated to dryness, and the residue purified on silica gel eluting with 5% methanol in dichloromethane. The product from the column was triturated with ether to afford title compound as a colourless solid (160 mg).m/e 487 [M]30 1H NMR (400 MHz, DMSO) delta 7.51 (1H, dd), 7.48-7.44 (1H, m), 7.41-7.32 (2H, m), 7.32-7.27 (1H, m), 7.10 (1H, dd), 6.97 (1H, dd), 5.17-5.13 (1H, m), 3.95-3.88 (1H, m), 3.65-3.56 (1H, m), 3.50-3.40 (4H, m), 3.33-3.26 (1H, m), 3.24-3.16 (1H, m), 3.04-2.97 (2H, m), 2.51-2.42 (2H, m), 2.41-2.32 (2H, m), 2.31-2.23 (1H, m), 2.04-1.83 (4H, m), 1.62 (3H, s), 1.56-1.38 (6H, m).; Preparation of Example 57 Bromide; (3R)-1-[2-(3-Chlorophenyl)ethyl]-3-{[2-piperidin-1-yl-2-(2-thienyl)propanoyl]oxy}-1-azoniabicyclo[2.2.2]octane bromide (Isomer 1) Crystalline Form A; (3R)-1-Azabicyclo[2.2.2]oct-3-yl 2-piperidin-1-yl-2-(2-thienyl)propanoate (Example 57b, Isomer 1, 0.5 g) in acetonitrile (3 mL) was treated with 1-(2-bromoethyl)-3-chlorobenzene (0.35 g) and the mixture stirred and heated at 80 C. for 4 h. The mixture was concentrated to dryness, and the residue purified on silica gel eluting with 5% methanol in dichloromethane. The product from the column was triturated with diethyl ether to afford title compound as a colourless solid (160 mg).m/e 487 [M]+ 1H NMR (400 MHz, DMSO) delta 7.51 (1H, dd), 7.48-7.44 (1H, m), 7.41-7.32 (2H, m), 7.32-7.27 (1H, m), 7.10 (1H, dd), 6.97 (1H, dd), 5.17-5.13 (1H, m), 3.95-3.88 (1H, m), 3.65-3.56 (1H, m), 3.50-3.40 (4H, m), 3.33-3.26 (1H, m), 3.24-3.16 (1H, m), 3.04-2.97 (2H, m), 2.51-2.42 (2H, m), 2.41-2.32 (2H, m), 2.31-2.23 (1H, m), 2.04-1.83 (4H, m), 1.62 (3H, s), 1.56-1.38 (6H, m).
The synthetic route of 3-Chlorophenethyl Bromide has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Ford, Rhonan; Mete, Antonio; Millichip, Ian; Teobald, Barry; US2010/113510; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics