Electric Literature of 138385-59-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 138385-59-8, name is 4-Iodo-2,6-dimethylaniline hydrochloride belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
(Z)-Methyl 3-(4-amino-3,5-dimethylphenyl)-2-(benzyloxycarbonyl)acrylate.; A 2 L round bottom flask was charged 4-iodo-2,6-dimethylbenzenaminehydrochloride salt (55 g, 194 mmoles), methyl 2-(benzyloxycarbonyl)acrylate (59.2 g, 252 mmoles), tetrabutylammonium chloride (59.2 g, 213 mmoles), palladium (II) acetate (4.34 g, 19.4 mmoles), and tetrahydrofuran (1.2 L, degassed by a flow of nitrogen for 30 min). The mixture was stirred so that a suspension was formed and then degassed by a flow of nitrogen for 30 min. Triethylamine (1 10 mL, 789 mmoles) was added and the resulting mixture was heated at reflux for 3 h. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, washed with tetrahydrofuran (2 x 100 mL), and concentrated. The residue was dissolved in dichloromethane, washed with water (3X) and brine (2X), dried over sodium sulfate, and concentrated. Flash chromatography (silica gel, using 1 :9 ethyl acetate/dichloromethane) gave a tan solid. The solid was recrystallized from warm methanol (210 mL) and water (100 mL). The mixture was held at room temperature overnight, then at 0C for 2 h, and finally at -15C for 2 h. The resulting solid was filtered, washed with ice cold 1 : 1 methanol/water, and dried under high vacuum overnight to give 44.7 g (65%) as a light tan solid which was a mixture of Z/E isomers (73:27). XH-NMR (DMSO-d6) delta, 2.05 (s, 6 H), 3.61 (s, 0.8 H), 3.68 (s, 2.2 H), 5.00 (s, 0.54 H), 5.13 (s, 1.46 H), 5.24 (s, 2 H), 7.40-7.21 (m, 8 H), 8.51 (s, 0.27 H), 8.79 (s, 0.73 H); 1 jC-NMR (DMSO-d6) delta 17.8, 51.7, 65.3, 1 19.4, 120.0, 120.3, 127.3, 127.7, 128.3, 130.9, 135.8, 137.2, 146.9, 154.7, 166.0.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Iodo-2,6-dimethylaniline hydrochloride, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHATURVEDULA, Prasad V.; DUBOWCHIK, Gene M.; MACOR, John E.; WO2011/123232; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com