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Background and overview
O-bromofluorobenzene is an organic intermediate, which can be prepared from o-fluoroaniline through diazotization reaction. 2-Bromofluorobenzene can be used to prepare 2-fluoro-5-bromobenzonitrile, and 2-fluoro-5-bromobenzonitrile as an important pharmaceutical intermediate has a wide range of uses, such as synthesis 1) for the treatment of inflammation and immunity A new type of cinnamamide compound (2?cumyl) [2?cyano?4?(E?((4?morpholine)carbonyl)ethyl)phenyl]sulfide, 2) for cancer chemotherapy Thieno[3,2?d]?pyrimidine?4?ketone compounds, which can inhibit the activity of Pim kinase, 3) indazole compounds, which can be used as glucokinase activators for the treatment of diabetes and obesity , 4) Quinoline derivatives used as HIV inhibitors.
preparation
Add 70g 40% HBr, 70ml H2O, 11.1g o-fluoroaniline to a 250ml flask, and heat to 70-80°C for reaction. Cool down to 40-50°C, add 7.2g CuBr, and stir well. Add dropwise a solution of 8.3g NaNO2 and 25ml H2O, and keep the reaction at the end after dripping. Reduce to room temperature, pour into 200ml H2O, separate the organic layer, wash the organic layer close to neutral, dry with anhydrous Na2SO4, filter with suction, and then distill under reduced pressure to obtain 14.4g of light yellow transparent liquid o-fluorobromobenzene, the yield is 82.8% .
application
2-Bromofluorobenzene can be used to prepare 2-fluoro-5-bromobenzonitrile. The method is as follows:
Add 40ml of DMF, 11.7g of CuCN, and 17.4g of o-fluorobromobenzene to a 250ml flask, heat to 150°C, and react for 5h. After the reaction, steam distilled to obtain 7.26 g of yellow transparent liquid o-fluorobenzonitrile with a yield of 60%.
Add 20ml of concentrated H2SO4 and 6.05g of o-fluorobenzonitrile to a 100ml flask, add 8.85g of NBS in batches under stirring, and react at room temperature for 2h after adding NBS. After the reaction, it was poured into 100ml of ice water under stirring to precipitate solids, filtered with suction, washed with water, and recrystallized with anhydrous EtOH to obtain 7.96g of white crystalline product 2-fluoro-5-bromobenzonitrile, with a yield of 80%.
