As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 191348-14-8 name is 2-Iodo-4-methoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 191348-14-8
General procedure: General procedure for the synthesis of N-Boc Indoles: (Step 1) A mixture of o-iodoaniline (10 mmol), CuI (19.5 mg, 0.1 mmol, 1.0 mol%) and Pd(PPh3)2Cl2 (140.4 mg, 0.2 mmol, 2.0 mol%) in dry NEt3 (20 mL) was added into a three-neck flask (50 mL) and stirred at room temperature in nitrogen atmosphere. Followed by dropwise addition of alkyne (12.0 mmol, 1.2 equiv) and the mixture was stirred at room temperature (rt) until complete disappearance of the o-iodoaniline (TLC monitoring). Then saturated NH4Cl solution was added and the mixture was stirred for another 30 minutes. The mixture was extracted with dichloromethane (30 mL¡Á3) and the organic layer was washed with brine solution, dried over anhydrous Na2SO4, the solvent was evaporated under reduced pressure and the residue was purified by column chromatography. (Step 2) The purified product of Step 1 and PdCl2 (5.0 mol%) in CH3CN (25 mL) was heated at 85 C in a round-bottom (50 mL) under nitrogen atmosphere until complete disappearance of the starting material (TLC monitoring). The mixture was allowed reach to rt, the solvent was evaporated under reduced pressure and the residue was purified with by column chromatography. (Step 3) The product of Step 2 and (Boc)2O (1.1 equiv) in dry CH3CN (20 mL) was (50 mL) was stirred at room temperature in a round-bottom (50 mL). Then 4-(N,N-dimethylamino)pyridine (3.0 mol%) was added and the mixture was stirred at room temperature until complete disappearance of the starting material (TLC monitoring). Then the solvent was evaporated under reduced pressure and the residue was purified by column chromatography.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-4-methoxyaniline, and friends who are interested can also refer to it.
Reference:
Article; Zhou, Xiao-Yu; Chen, Xia; Wang, Liang-Guang; Yang, Dan; Li, Zhi; Synthesis; vol. 49; 16; (2017); p. 3662 – 3669;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com