Electric Literature of 103273-01-4, These common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, 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.
General procedure: A mixture of 2-bromo-4-tert-butylaniline (2.28 g, 10 mmol), 2,5-dimethoxytetrahydrofuran (4.2 g, 30 mmol) and glacial acetic acid (150 mL) in a 250 mL three-necked RB flask was refluxed under nitrogen for 17 h. Then it was cooled, poured into aq. HCl (200 mL) and extracted with CH2Cl2, then combined organic phase was washed with water and dried over MgSO4. After workup, the crude product was purified by column chromatography (PE) to afford 3ac as a white powder (1.97 g, 52 %); Rf = 0.28 (PE); m. p. 138 -140 C; 1H-NMR (CDCl3, 300 MHz) delta: 8.18 (d, J = 7.5 Hz, 2H), 7.85 (d, J = 11.4 Hz, 1H), 7.55 (d, J = 10.8 Hz, 1H), 7.42 (m, 3H), 7.29 (m, 2H), 7.12 (d, J = 7.8 Hz, 2H), 1.45 (s, 9H); 13C-NMR (CDCl3, 100 MHz) delta: 153.85, 141.01, 133.88, 131.20, 130.45, 126.03, 125.89, 123.42, 123.20, 120.35, 119.89, 110.18, 36.06, 31.32.
The synthetic route of 103273-01-4 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Lv, Jun; Liu, Qiancai; Tang, Jie; Perdih, Franc; Kranjc, Kristof; Tetrahedron Letters; vol. 53; 39; (2012); p. 5248 – 5252;,
Bromide – Wikipedia,
bromide – Wiktionary