Adding a certain compound to certain chemical reactions, such as: 191348-14-8, name is 2-Iodo-4-methoxyaniline, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 191348-14-8, Quality Control of 2-Iodo-4-methoxyaniline
m-Iodophenol (5.5 g, 25 mmol) was dissolved in water containing KOH (1.4 g, 25 mmol). A cold solution of diazotized sulfanilic acid (5.1 g, 27.5 mmol) was added to the mixture with stirring at rt for 30 min followed by the addition of sodium hydrosulfite (12 g, 69 mmol). The colour of the solution was changed immediately upon the addition of sodium hydrosulfite and the solution was stirred at 45 C for 20 min. Diethyl ether was added to the mixture, the mixture was filtered and the filtrate was concentrated. The solid was recrystallized from hot water to yield needles. Methyl iodide was added (0.98 mL, 15.7 mmol) to 4-amino-3-iodophenol (3.71 g, 15.8 mmol) in DMF (70 mL) in the presence of Cs2CO3 (13.45 g, 41.3 mmol). The reaction was left at rt for 48 h. The mixture was then diluted with water, extracted with diethyl ether, the combined organic extracts were washed with water, dried over Na2SO4, filtered and concentrated. The product was purified by silica gel column chromatography (PE/EtOAc 9:1) and obtained 4-methoxy-2-iodoaniline (15) as a light brown oil (3.36 g, 54%) from m-iodophenol.To a solution of 4-methoxy-2-iodoaniline (3.0 g, 12.0 mmol) in THF (20 mL) was added di-tert-butyl dicarbonate (3.15 g, 14.5 mmol). The reaction mixture was refluxed for 2 days then quenched with water (15 mL). The solution was extracted with Et2O (3×20 mL) and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated. The crude mixture was purified by silica gel column chromatography (2% EtOAc in PE) to yield N-Boc-2-iodo-4-methoxy aniline as a light brown solid (3.72 g, 89%). 1H NMR (500 MHz, CDCl3, delta): 7.82 (s, 1H), 7.29 (d, J=3.0 Hz, 1H), 6.88 (dd, J=9.0, 3.0 Hz, 1H), 6.53 (s, 1H), 3.75 (s, 3H), 1.52 (s, 9H); 13C NMR (125 MHz, CDCl3, delta): 156.21, 153.21, 132.54, 123.89, 122.24, 115.05, 80.87, 55.85, 28.48; IR (KBr, cm-1): 3322, 2983, 1718; HRMS (ESI): (M+Na)+ calcd for +C12H163INNaO 372.0067, found 372.0071.
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Reference:
Article; Jana, Goutam Kumar; Sinha, Surajit; Tetrahedron; vol. 68; 35; (2012); p. 7155 – 7165;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com