Electric Literature of 153505-37-4, A common heterocyclic compound, 153505-37-4, name is 4-Bromo-5-fluorobenzene-1,2-diamine, molecular formula is C6H6BrFN2, 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.
2-Amino-4-bromo-5-fluoroaniline (9.2 g, 45 mmol) was dissolved in acetic acid (190 ml) and water (260 ml) before sodium nitrite (3.1 g, 45 mmol) in 10 mL of water was added dropwise. The reaction was stirred at room temperature for 1 hour before the solution was cooled to 0 C and ammonium hydroxide was added to adjust the pH to ~11. The mixture was extracted with EtOAc (3 x 500 mL), and the combined organics were dried over sodium sulfate, filtered, and concentrated to a brown solid (9.0 g, 71 %). MS (m/z) 215.9, 217.9 (M+, M+2+). 5-bromo-6-fluoro-1H-1,2,3-benzotriazole (1.0 g, 4.6 mmol), copper(I) iodide (88 mg, 0.46 mmol), and sodium iodide (2.8 g, 19 mmol) were added to a flask which was subsequently purged with argon. 1,4-Dioxane (7.0 ml) was added followed by N,N’-ethylenediamine (0.10 ml, 0.93 mmol). The reaction was heated to 120 C overnight. It was cooled to room temperature and partitioned between water and EtOAc. The organics were collected and the aqueous layer was back-extracted with EtOAc. The combined organics were dried over sodium sulfate, filtered, and concentrated (420 mg, 35 %). MS (m/z) 263.9 (M+H+).
The synthetic route of 153505-37-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GlaxoSmithKline Intellectual Property Development Limited; BURY, Michael, Jonathan; CASILLAS, Linda, N.; CHARNLEY, Adam, Kenneth; DEMARTINO, Michael, P.; DONG, Xiaoyang; HAILE, Pamela, A.; HARRIS, Philip, Anthony; LAKDAWALA SHAH, Ami; KING, Bryan, W.; MARQUIS, Robert, W., Jr.; MEHLMANN, John, F.; ROMANO, Joseph, J.; SEHON, Clark, A.; EIDAM, Patric; EP2566477; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary