Preparation and application of 4-bromo-2,6-dimethylphenol_Kain Industrial Additive

Background and overview^[1]

4-Bromo-2,6-dimethylphenol is an aryl halide. In organic synthesis, aryl halides are widely present in many biologically active natural products. At the same time, aryl halides, as important organic synthesis intermediates, greatly improve the efficiency of organic synthesis.

Preparation^[1]

Preparation of 4-bromo-2,6-dimethyl-phenol: Take a 25mL Schlenk reaction tube, add 61mg of 2,6-dimethyl-phenol, 48% hydrobromic acid aqueous solution 92.7 mg, 39 μL of dimethyl sulfoxide, 2 mL of ethyl acetate, stir at 60°C for 3 hours. After the reaction was completed, 96 mg of 4-bromo-2,6-dimethyl-phenol was obtained by column chromatography, with a yield of 95%. ¹HNMR (400MHz, CDCl₃) δ7.02 (s, 2H), 4.61 (s, 1H), 2.22 (s, 6H).¹³CNMR(100MHz, CDCl₃)δ151.3, 131.0, 125.2, 112.0, 15.7.

Application^[2]

CN201310456775.5 reported that 4-bromo-2,6-dimethylphenol can be used to prepare a m-diarene-polysubstituted pyrimidine derivative N-(4′-cyanophenyl)-2- (2′,6′-Dimethyl-4′-bromo-phenoxy)-5-nitropyrimidine. Metadiarene-polysubstituted pyrimidine derivatives show significant antiviral activity and high selectivity in cell tests (MT-4 cells) that inhibit HIV replication. Metadiarene-polysubstituted pyrimidine derivatives have great development value. New structural modifications and in-depth research on the compounds of the present invention will help develop new anti-HIV drugs.

References

[1] CN201510056285.5 Cheap and efficient preparation method of aryl halide

[2] [Chinese invention, Chinese invention authorization] CN201310456775 .5 Meta-diarene-polysubstituted pyrimidine derivatives and their preparation methods and applications