Related Products of 1435-53-6,Some common heterocyclic compound, 1435-53-6, name is 2,4-Dibromo-1-fluorobenzene, molecular formula is C6H3Br2F, 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: 8.10 1-(2′,5′-Dimethoxyphenyl)-3-(2′,5′-dimethoxyphenyl)-4-fluorobenzene (11j): Starting with 10 (100 mg, 0.39 mmol), Cs2CO3 (253 mg, 0.78 mmol), Pd(PPh3)4 (3 mol%), 2,5-dimethoxyphenylboronic acid (158 mg, 0.85 mmol) and 1,4-dioxane (4 mL), 11j was isolated as a colorless solid (91 mg, 65%). Mp 149-150 C. 1H NMR (300 MHz, CDCl3): delta = 3.68 (s, 3H, CH3), 3.69 (s, 3H, OCH3), 3.71 (s, 6H, OCH3), 6.70-6.80 (m, 6H, ArH), 7.04-7.10 (m, 1H, ArH), 7.40-7.45 (m, 2H, ArH). 13C NMR (75 MHz, CDCl3): delta = 55.8 (2OCH3), 56.3 (OCH3), 56.4 (OCH3), 112.4 (CH), 112.6 (CH), 113.2 (CH), 114.2 (CH), 115.1 (d, J = 22.6 Hz, CH), 116.7 (CH), 117.1 (CH), 125.6 (d, J = 16.4 Hz, C), 126.0 (C), 130.3 (d, J = 7.6 Hz, CH), 130.5 (C), 132.8 (d, J = 4.0 Hz, CH), 134.0 (d, J = 3.5 Hz, C), 150.7 (C), 151.3 (C), 153.5 (C), 153.8 (C), 159.3 (d, JCF = 249.0 Hz, CF). 19F NMR (282 MHz, CDCl3): delta = -116.3 (CF). IR (ATR, cm-1): , 3021 (w), 2948 (w), 2832 (w), 1582 (w), 1486 (s), 1463 (m), 1407 (m), 1381 (m), 1295 (m), 1264 (m), 1220 (s), 1174 (s), 1113 (m), 1049 (s), 1023 (s), 915 (w), 855 (m), 803 (m), 755 (w), 706 (s), 5651 (w), 568 (w), 507 (w), 468 (w) cm-1. MS (EI, 70 eV): m/z (%) = 368 (100) [M]+, 339 (12), 338 (57), 169 (12). HRMS (ESI) calcd. for C22H22O4F [M + H]+: 369.14966; found 369.14871.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Dibromo-1-fluorobenzene, its application will become more common.
Reference:
Article; Sharif, Muhammad; Maalik, Aneela; Reimann, Sebastian; Feist, Holger; Iqbal, Jamshed; Patonay, Tamas; Villinger, Alexander; Langer, Peter; Journal of Fluorine Chemistry; vol. 146; (2013); p. 19 – 36;,
Bromide – Wikipedia,
bromide – Wiktionary