Adding a certain compound to certain chemical reactions, such as: 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 16518-62-0, SDS of cas: 16518-62-0
In a two-necked 200 mL round-bottom flask, Mg turnings (5.30 g, 216 mmol, 10.0 equiv) were flame-dried under vacuum. Upon cooling to room temperature, THF (55 mL), 3-bromo-N,N-dimethylaniline (6.50 g, 32.4 mmol, 1.50 equiv) as a solution in THF (55 mL) and a crystal of I2 were added. The flask was fitted with a reflux condenser and the solution vigorously stirred. Once the resulting exotherm had subsided, the reaction mixture was heated to reflux (70 ¡ãC) for 1h. This Grignard reagent was then allowed to cool to room temperature and added to a cooled solution of 2-bromobenzaldehyde (4.00 g, 21.6 mmol, 1.00 equiv) in THF (32 mL) at 0 ¡ãC via cannula over 10 mm. The reaction mixture was then allowed to reach room temperature and stirred for 12 h and quenched with sat. aq. NH4Cl (75 mL). The aqueous phase was then extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography on silica (1percent to 5percent EtOAc in hexanes) provided the desired (2-bromophenyl)(3-(dimethylamino)phenyl)methanol (S8) (6.36 g, 20.8 mmol, 96percent yield) a yellow viscous oil: Rf 0.4 (20percent EtOAc in hexanes); 1H NMR (500 MHz, CDC13) oe 7.59 (dd, J= 7.7, 1.6 Hz, 1 H), 7.53 (dd, J= 7.9, 1.1 Hz, 1 H), 7.33 (td, J= 7.5, 1.0 Hz, 1 H), 7.20 (t, J= 7.9, 1 H), 7.13 (td, J= 7.7, 1.6 Hz, 1 H), 6.84 (bs, 1 H),6.72 (d, J= 7.5, 1 H), 6.66 (dd, J= 8.2, 2.2 Hz, 1 H), 6.16 (s, 1 H), 2.93 (s, 6 H), 2.38 (bs, 1 H); 13C NMR (125 MHz, CDCl3) oe 150.8, 143.3, 142.9, 132.9, 129.3, 129.1, 128.7, 127.8, 123.1,115.3, 112.2, 111.4, 75.3, 40.8; IR (neat) 3392 (bs), 2917 (s), 2848 (s), 1604 (s), 1498 (s), 1437 (s), 1353 (s), 1018 (m), 996 (s), 744 (s) cm?; HRMS (ES) m/z calculated for C15H17NOBr [M+H] 306.0494, found 306.0492.
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Reference:
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; HOYE, Adam, T.; KIM, Won-suk; MARTINEZ-SOLORIO, Dionicio; SMITH, Amos, B.; SANCHEZ, Luis; TONG, Rongbiao; NGUYEN, Minh, Huu; WO2013/185021; (2013); A2;,
Bromide – Wikipedia,
bromide – Wiktionary