Method for preparing biaryl compound by using aryl sulfuryl fluoride as raw material
A technology of arylsulfonyl fluoride and arylsulfonyl, which is applied in the field of organic chemical synthesis, can solve the problems of expensive halogenated aromatic hydrocarbons, and achieve the effects of reducing production costs, wide application prospects, and simple reaction and separation
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Embodiment 1
[0014] Embodiment 1: the preparation of 4-nitrobiphenyl
[0015] In air, sequentially add 0.5mmol of 4-nitrophenylsulfonyl fluoride, 0.6mmol of phenylboronic acid, 1.5mmol of triethylamine, 0.005mmol of palladium acetate, 4mL of absolute ethanol, and 4mL of water into a 10mL circle in the bottom flask. The reaction was magnetically stirred at 25°C. After 4 hours of reaction, 15 mL of saturated brine was added to the round bottom flask to quench the reaction, the mixture was extracted with 3×15 mL of ethyl acetate, the organic phases were combined after extraction, and the organic phases were concentrated under reduced pressure to obtain The crude product was subjected to column chromatography with petroleum ether as the eluent to obtain the final product. The structure of the product was identified by H-NMR and mass spectrometry, and the separation yield reached 92%.
Embodiment 2
[0016] Embodiment 2: the preparation of 4-methylbiphenyl
[0017] In air, sequentially add 0.5mmol of 4-methylphenylsulfonyl fluoride, 0.6mmol of phenylboronic acid, 1.5mmol of triethylamine, 0.005mmol of palladium acetate, 4mL of absolute ethanol, and 4mL of water into a 10mL circle in the bottom flask. The reaction was magnetically stirred at 25°C. After 4 hours of reaction, 15 mL of saturated brine was added to the round bottom flask to quench the reaction, the mixture was extracted with 3×15 mL of ethyl acetate, the organic phases were combined after extraction, and the organic phases were concentrated under reduced pressure to obtain The crude product was subjected to column chromatography with petroleum ether as the eluent to obtain the final product. The structure of the product was identified by H-NMR and mass spectrometry, and the separation yield was 91%.
Embodiment 3
[0018] Embodiment 3: the preparation of 4-methoxybiphenyl
[0019] In air, sequentially add 0.5mmol of 4-methoxyphenylsulfonyl fluoride, 0.6mmol of phenylboronic acid, 1.5mmol of triethylamine, 0.005mmol of palladium acetate, 4mL of absolute ethanol, and 4mL of water into 10mL in a round bottom flask. The reaction was magnetically stirred at 25°C. After 4 hours of reaction, 15 mL of saturated brine was added to the round bottom flask to quench the reaction, the mixture was extracted with 3×15 mL of ethyl acetate, the organic phases were combined after extraction, and the organic phases were concentrated under reduced pressure to obtain The crude product was subjected to column chromatography using petroleum ether as the eluent to obtain the final product. The structure of the product was identified by H-NMR and mass spectrometry, and the separation yield reached 94%.
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