Preparation and application background and overview of 2-bromomethyl-4-fluorophenylboronic acid
2-Bromomethyl-4-fluorophenylboronic acid can be used as a pharmaceutical synthesis intermediate. It can be prepared by reacting 4-fluoro-2-methylphenylboronic acid as a raw material under the action of bromine and tetrachloromethane. have to.
Preparation and application of 2-bromomethyl-4-fluorophenylboronic acid
1) Add 1.8 g (11.7 mmol) 4-fluoro-2-methylphenylboronic acid and 20 mL anhydrous tetrachloromethane into a 50 mL two-necked round-bottomed flask equipped with a connected dropping funnel, and stir the mixture. white suspension and flush with nitrogen through a syringe for 15 minutes;
2) Add 12.1 mmol of dry elemental bromine into the funnel, dissolve it in 5 mL of dry cold tetrachloromethane, install a 500-watt halogen bulb at a distance of 10 cm, irradiate the mixture and heat to reflux, at Slowly add the bromine solution to the suspension drop by drop within 60 minutes;
3) Stop the irradiation, stir the mixture for another 60 minutes, and flush the flask with nitrogen for 30 minutes to remove excess bromine and hydrogen bromide;
4) Filter the reaction mixture through a glass funnel to remove insoluble educts and oxidation products (wash with a small amount of cold CCl4), store the filtrate in the refrigerator overnight, decant to separate the crystals, And wash with cold CCl4;
5) Concentrate the residual filtrate to 10 mL, store in the refrigerator to obtain crystals, then wash with cold CCl4, and recrystallize the combined crystallization grades with CCl4 The crystals were dried under high vacuum at 30°C to obtain 2-bromomethyl-4-fluorophenylboronic acid.
Preparation and application of 2-bromomethyl-4-fluorophenylboronic acid
2-Bromomethyl-4-fluorophenylboronic acid can be used to prepare luminescent dyes with the following general formula. The luminescent dye can be used to prepare polymers and thus sensors for detecting analytes. The sensor may be implanted in the subcutaneous tissue of the mammalian subject to measure blood glucose concentration in the mammalian subject.
References
[1] Jörg Axthelm, Helmar Görls, Schubert U S, et al. Fluorinated Bmethoxypyridine oronic Acid-Appended Bipyridinium Sa calcium carbonate for Diol Recognition and Discrimination via 19F NMR Barcodes[J]. Journal of the American Chemical Society, 2015, 137(49).
[2] [Invented in China] CN201780080940.8 near-infrared glucose sensor
