Synthesis
1-BROMO-2,4,6-TRIISOPROPYLBENZENE was synthesized by reacting 1,3,5-triisopropylbenzene with PIFA-TMSBr in the presence of a rare gas. The synthesis method is as follows:
In a multiple reaction tube under an argon atmosphere, 1.8 mmol PhI(OTFA)2·(PIFA) (490 mg, 1 equivalent) was dissolved in 12 mL of dry dichloromethane solution. Then, 2.44 mmol (2.0 equivalent) of TMSBr was added to the solution. The clear solution turned into a clear orange color. Then, 250 mg (1.22 mmol) of 1,3,5-triisopropylbenzene was added, and the reaction was carried out at room temperature. After the reaction was completed, the solution was poured into water and extracted with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered, and the organic solvent was evaporated and concentrated. The crude oil was then concentrated under high vacuum to obtain 280 mg of 2-bromo-1,3,5-triisopropylbenzene, with a yield of 81%.
Uses
1-Bromo-2,4,6-triisopropylbenzene can be used in the synthesis of 1-fluoro-2,4,6-triisopropylbenzene, a fluorine-substituted aromatic building block for agrochemical synthesis and pharmaceutical production. It can also be used in the synthesis of di-2,4,6-triisopropylphenyl diselenide via reaction with metallic selenium in the presence of
tertiary-butyl lithium.
