4-Iodo-1,2-dimethylbenzene

Chemical Properties

clear yellow to red-brown liquid

Uses

1-Iodo-3,4-dimethylbenzene (4-iodo-o-xylene, 3,4-dimethyliodobenzene) may be used in the synthesis of the following:

• 3-arylacrylamide
• 3,3-diaryl substituted acrylamide
• 3-arylpropylamine
• di-tert-butyl 1-(3,4-dimethylphenyl)hydrazine-1,2-dicarboxylate
• 2,3,7,8-tetramethyldibenzofuran
• N-(3-(3,4-Dimethylphenyl)-2-phthalimidopropionyl)-2-methylthioaniline

General Description

1-Iodo-3,4-dimethylbenzene (4-iodo-o-xylene, 3,4-dimethyliodobenzene) is an aryl halide. Its synthesis, NMR and IR spectra has been reported. Its nitration reaction and copper catalyzed trifluoromethylation reaction has been studied.

Synthesis

95-47-6

31599-61-8

GENERAL STEPS: To a solution of 1,2-dimethylbenzene (o-xylene, 0.106 g, 1 mmol) in acetonitrile (10 mL) was sequentially added iodine (1 mmol, 0.126 g) and polymer-loaded periodate (0.6 g, 1.05 mmol). The reaction mixture was stirred at 40 °C for 1 hour. The progress of the reaction was monitored by thin layer chromatography (TLC) and the unfolding agent was a solvent mixture of ethyl acetate and hexane (1:9, v/v). After completion of the reaction, the mixture was cooled to room temperature and filtered. Excess iodine in the filtrate was removed by adding sodium bisulfite solution (1 M) dropwise. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and evaporated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography, the eluent being a solvent mixture of hexane and ethyl acetate. The final product was 3,4-dimethyl iodobenzene in 95% isolated yield with a boiling point of 235 °C (literature value: 234 °C).

References

[1] Bulletin of the Chemical Society of Ethiopia, 2014, vol. 28, # 2, p. 305 - 308
[2] Tetrahedron Letters, 2011, vol. 52, # 18, p. 2413 - 2414
[3] Advanced Synthesis and Catalysis, 2005, vol. 347, # 15, p. 1925 - 1928
[4] Patent: EP1595862, 2005, A1. Location in patent: Page/Page column 9
[5] European Journal of Organic Chemistry, 2017, vol. 2017, # 22, p. 3234 - 3239