4-Bromo-2,3-dimethylphenol

Synthesis

GENERAL METHODS: 2,3-Dimethylphenol (1 mmol) was dissolved in acetonitrile (5 mL), OXBTEATB (0.233 g, 0.5 mmol) was added, and the reaction was stirred at room temperature until the appropriate time (Table 1). The reaction process was monitored by thin layer chromatography (TLC) (eluent ratio: hexane/ethyl acetate = 5/1). Upon completion of the reaction, OXBTEATB was removed by filtration, and the filtrate was transferred to a partition funnel and extracted sequentially with water (15 mL) and dichloromethane (20 mL). The organic layers were combined and dried with anhydrous Na2SO4, followed by concentration on a rotary evaporator to remove solvent. The crude product was purified by silica gel column chromatography, the eluent being a solvent mixture of hexane and ethyl acetate. To regenerate the reagents, the resulting white solid was treated with liquid bromine. The structures of all products were analyzed by melting point determination or 1H NMR spectroscopy and confirmed by comparison with data reported in the literature [29a-29e].

References

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[4] Synthetic Communications, 2010, vol. 40, # 6, p. 868 - 876
[5] Tetrahedron, 2003, vol. 59, # 18, p. 3201 - 3217