ChemicalBook CAS DataBase List 4-IODO-2-METHYLANILINE

4-IODO-2-METHYLANILINE synthesis

6synthesis methods

Product Name:4-IODO-2-METHYLANILINE
CAS Number:13194-68-8
Molecular formula:C7H8IN
Molecular Weight:233.05

583-75-5

13194-68-8

General procedure for the synthesis of 4-iodo-2-methylaniline from 2-methyl-4-bromoaniline: the aromatic Finkelstein reaction is used. Since copper(I) iodide is sensitive to moisture and oxygen, the reaction is carried out under argon protection using the standard Schlenk technique. The procedure is as follows: 2-methyl-4-bromoaniline, NaI (2 equiv., relative to bromine exchange) and CuI (5 mol%, relative to bromine exchange) are added to a two-necked pear-shaped flask equipped with a reflux condenser. N,N'-dimethylethylenediamine (L1) or N,N'-dimethyl-1,2-cyclohexanediamine (L2) (10 mol%, relative to bromine exchange) and anhydrous 1,4-dioxane (0.5 mL per 1 mmol NaI) were subsequently added. The resulting suspension was heated to 110°C and reacted for 18 hours. After completion of the reaction, it was cooled to room temperature and the mixture was poured into a 25% ammonia solution. The blue solution was diluted with deionized water until doubled in volume and extracted three times with dichloromethane. If 2,2'-bipyridine was used as the ligand, the combined organic phases were additionally washed with aqueous EDTA; otherwise, the combined organic phases were washed with saturated saline only and dried with anhydrous magnesium sulfate. The solvent is removed by concentration under reduced pressure to give pure 4-iodo-2-methylaniline. If necessary, the crude product can be further purified by column chromatography or recrystallization.

583-75-5
313 suppliers
$5.00/1g

13194-68-8
220 suppliers
$6.00/1g

Yield: 90%

Reaction Conditions:

with copper(l) iodide;sodium iodide;N,N`-dimethylethylenediamine in 1,4-dioxane at 110; for 18 h;Inert atmosphere;Schlenk technique;Finkelstein Reaction;

Steps:

Aromatic Finkelstein Reaction; General Procedure
Aromatic Finkelstein Reaction; General ProcedureThe reaction was carried out under argon using standard Schlenktechniques due to the moisture and oxygen sensitivity of the copper(I) iodide. A two-neck pear-shaped flask equipped with a refluxcondenser was charged with the (het)aryl bromide starting material,NaI (2 equiv per bromine to exchange), and CuI (5 mol% per bromineto exchange). N,N′-Dimethylethylenediamine (L1) or N,N′-dimethyl-1,2-cyclohexanediamine (L2) (10 mol% per bromine toexchange) and anhydrous 1,4-dioxane (0.5 mL per 1 mmol NaI)were added. The resulting suspension was heated to 110 °C for 18h. After cooling to r.t., the mixture was poured into aq 25% NH3 solution.The blue solution was diluted to a doubled volume with H2Oand was extracted three times with CH2Cl2. In the case of the 2,2′-bipyridines, the combined organic phases were additionally washedwith aq EDTA solution. Otherwise, the combined organic phaseswere solely washed with brine and dried with MgSO4. The solventwas removed under reduced pressure to give the desired product inpure form. If needed, the crude product can be purified by columnchromatography or recrystallization.

References:

Meyer-Eppler, Georg;Kuechler, Lea;Tenten, Christina;Benkhaeuser, Christian;Brueck, Stefanie;Luetzen, Arne [Synthesis,2014,vol. 46,# 8,art. no. SS-2013-Z0057-OP,p. 1085 - 1090]

95-53-4 Synthesis