Electric Literature of 103273-01-4, A common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, molecular formula is C10H14BrN, its 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.
To a suspension of 4-trifluoromethylbenzoic acid (420 mg, 2.2 mmol) in dichloromethane (5 mL) was added N,N-dimethylformamide (1 drop) followed by oxalyl chloride (225 muL, 2.6 mmol) at 0 C. The mixture was warmed to room temperature and stirred for 4 hours before the volatile components were removed under a stream of nitrogen. The crude acid chloride was taken up in dichloromethane (2 mL) and added to a cooled solution of the aniline 39 (500 mg, 2.2 mmol) in dichloromethane (10 mL) and the mixture was stirred for 16 hours at room temperature. The reaction mixture was diluted with dichloromethane (20 mL), washed with saturated aqueous sodium hydrogen carbonate solution (2 x 20 mL) and saturated aqueous ammonium chloride solution (2 x 20 mL), dried over anhydrous magnesium sulfate and concentrated. The crude solid was purified by flash column chromatography using ethyl acetate, hexane (1:49 to 1:24) as an eluent and recrystallisation from isopropyl alcohol, water to obtain the title compound (660 mg, 75%) as a white solid, mp: 151.7-152.7 C; Rf: 0.63 (1:9 ethyl acetate, hexane); IR (vmax (film)): 3343, 2966, 1660, 1509, 1318, 1111, 1065 cm-1; 1H NMR (300 MHz, CDCl3): delta 1.31 (9H, s), 7.41 (1H, s), 7.79 (2H, d, J = 8.0 Hz), 8.04 (2H, d, J = 8.0 Hz), 8.31-8.45 (2H, m) ppm; 13C NMR (75 MHz, CDCl3): delta 31.4, 34.8, 114.1, 121.7, 123.6 (q, J = 270.0 Hz), 125.8, 126.2 (q, J = 3.6 Hz), 127.7, 129.4, 132.9, 133.2 (q, J = 31.2 Hz), 138.1, 149.6, 164.0 ppm; 19F NMR (282 MHz, CDCl3): delta -63.0 ppm; LRMS (+ESI) m/z: 422.0/424.0 ([M+Na]+ 100%); HRMS (ESI)+ Cald for C18H17BrF3NO [M+Na]+: 422.03378/424.03174, found 422.03396/424.03190.
The synthetic route of 103273-01-4 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Moir, Michael; Boyd, Rochelle; Gunosewoyo, Hendra; Montgomery, Andrew P.; Connor, Mark; Kassiou, Michael; Tetrahedron Letters; vol. 60; 36; (2019);,
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