Some common heterocyclic compound, 698-19-1, name is 1-(2-Bromophenyl)-N-methylmethanamine, molecular formula is C8H10BrN, 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. Formula: C8H10BrN
To a stirred solution of commercially available1-(2-bromophenyl)-N-methylmethanamine (565 mg, 2.8 mmol, 1.0 equiv.) and propiolic acid (0.21 mL,3.4 mmol, 1.2 equiv.) in CH2Cl2 (30 mL) was added DCC (700 mg, 3.4 mmol, 1.2 equiv.) at 0 C.Then, the reaction temperature was raised to r.t. After 1.5 h, the reaction mixture was diluted withCH2Cl2 (200 mL), and then washed with aq. 2N-HCl (5 mL) and sat. aq. NaHCO3 (20 mL). The organiclayer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude residue waspurified by column chromatography (silica gel, hexanesEtOAc 3:1) to yield 6c (675 mg, 95% yield) asan off-white solid; m.p. = 53.1 C; Rf = 0.3 (silica gel, hexanesEtOAc 2:1); IR (film) 3283, 3215, 3061,2926, 2107, 1644, 1401 cm-1; 1H-NMR (CDCl3, 1.3:1 atropisomeric mixture): delta = 7.59 (d, J = 8.0 Hz,1H, major), 7.56 (d, J = 8.0 Hz, 1H, minor), 7.35 (t, J = 7.5 Hz, 1H, major), 7.30 (t, J = 7.5 Hz, 1H, minor),7.19 (t, J = 7.8 Hz, 2H, major), 7.16 (d, J = 7.8 Hz, 2H, minor), 4.91 (s, 2H, major), 4.75 (s, 2H, minor),3.09 (s, 1H, major), 3.20 (s, 1H, minor), 2.94 (s, 3H, major), 3.18 (s, 3H, minor), ppm; 13C-NMR (CDCl3): delta= 154.4 (major), 154.2 (minor), 135.3 (major), 135.3 (minor), 133.5 (major), 133.3 (minor), 129.8 (major),129.6 (minor), 129.5 (minor), 128.4 (major), 128.3 (major), 128.2 (minor), 80.0 (minor), 79.4 (major),76.0 (minor), 75.9 (major), 54.9 (major), 50.0 (minor), 36.5 (minor), 32.7 (major) ppm; HRMS (EI): calcd. forC23H18ClNO [M+]: 250.9946, found 250.9944.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 698-19-1, its application will become more common.
Reference:
Article; Park, Sunhwa; Lee, Jiyun; Shin, Kye Jung; Oh, Euichaul; Seo, Jae Hong; Bunce, Richard A.; Molecules; vol. 22; 3; (2017);,
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