These common heterocyclic compound, 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, 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. Computed Properties of C8H6BrIO2
A mixture of methyl 5-bromo-2-iodobenzoate (3.849 g,11.259 mmol), phenanthren-1-ylboronic acid (4) (3 g,13.510 mmol), 2 M aqueous potassium carbonate (30 mL), and tetrakis(triphenylphosphine)palladium (0.651 g, 0.563 mmol) in THF (100 mL) and methanol (30 mL) was heated at reflux in a nitrogen atmosphere for 24 h. After the reaction mixture had been concentrated in vacuo, the resulting mixture was extracted with dichloromethane. The organic layer was washed with water and brine and dried using anhydrous sodium sulfate. The filtrate was concentrated in vacuo to give a crude mixture that was purified by column chromatography (SiO2, dichloromethane:hexane 1:4) to afford methyl 5-bromo-2-(phenanthren-1-yl)benzoate (3.5 g,8.945 mmol, 79%) as a white solid. 1H NMR (300 MHz, CDCl3): delta (ppm) 8.80 (d, J = 12.6 Hz, 2H), 8.22 (s, 1H), 7.88 (d, J = 7.8 Hz, 1H),7.77 (dd, J = 5.1, 1.8 Hz, 1H), 7.73-7.60 (m, 4H), 7.40 (dd, J = 7.8,1.5 Hz, 2H), 7.32 (d, J = 8.1 Hz, 1H), 3.41 (s, 3H). 13C NMR (75 MHz,CDCl3): delta (ppm) 166.4, 140.7, 139.0, 134.6, 133.5, 133.1, 131.7, 130.3,130.2, 130.0, 128.5, 127.2, 126.8, 126.7, 125.7, 123.9, 122.9, 122.4,121.5, 52.1. HR-Mass (EI+): calcd for C22H15BrO2 390.0255, found392.0257.
The synthetic route of Methyl 5-bromo-2-iodobenzoate has been constantly updated, and we look forward to future research findings.
Reference:
Article; Jeong, Seongjin; Hong, Jong-In; Dyes and Pigments; vol. 144; (2017); p. 9 – 16;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com