Reference of 25462-61-7, These common heterocyclic compound, 25462-61-7, name is 2,5-Dibromobenzene-1,4-diamine, 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.
In a Schlenk flask, 2,5-dibromo-1,4-phenylenediamine (500 mg, 1.88 mmol) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yI)-5-hexylthiophene 13 (2.21 g, 7.52 mmol)were charged under the protection of nitrogen. After adding 25 ml toluene, 10 mlethanol and 10 ml Cs2CO3 aqueous solution (2.0 mo/l), the mixture was degassedfor 30 mm. Pd(PPh3)4 (217.3 mg, 18.8 mmol) was added, then the mixture washeated to 80 C and stirred overnight. The reactant was poured into brine andextracted by dichloromethane for several times. The organic phase was dried overMg2504 and the solvent was evaporated in vacuo. The product was purified bychromatography on silica gel (petroleum ether/CH2CI2=1) to give product 14 asyellow flaky crystal (550 mg, 66%). 1H NMR (400 MHz, CDCI3, ppm): 0.90 (t, J = 7.02Hz, 6H), 1.46-1.23 (m, 12H), 1.76-1.64 (m, 4H), 2.82 (t, J = 7.65 Hz, 4H), 3.70 (br,4H), 6.79-6.73 (m, 4H), 7.02 (d, J 3.48 Hz, 2H). m/z[M+HJ calcd for C26H37N2S2441.2399; HR-ESI observed 441.2393. 13C NMR (100 MHz, CDCl3, ppm): 149.5,146.0, 133.3, 129.4, 128.9, 128.4, 122.2, 112.9, 32.0, 31.9, 30.7, 29.1, 22.8, 14.3.
The synthetic route of 25462-61-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MERCK PATENT GMBH; ZHANG, Fan; WANG, Xinyang; TANG, Ruizhi; FU, Yubin; ZHUANG, Xiaodong; FENG, Xinliang; WU, Dongqing; WO2015/43722; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary