Chemical Properties
Light yellow liquid
Uses
3-Bromo-2-fluoropyridine serves as a precursor for the synthesis of Benzo[b]pyrido[3,2-f][1,4]oxazepin-5(6H)-one via reaction with 2-aminophenol[2].
Synthesis
GENERAL METHOD: 2,3-Dichloropyridine (1.00 g, 6.76 mmol) was dissolved in DMSO (33.8 mL) at room temperature, followed by the addition of CsF (2.053 g, 13.51 mmol). The reaction mixture was stirred at 110 °C for 20 h in air. Upon completion of the reaction, the reaction mixture was quenched with ice water and extracted with EtOAc. The organic layer was separated, washed sequentially with water and brine, dried over anhydrous Na2SO4 and subsequently concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel as stationary phase and EtOAc in hexane as eluent) afforded 3-chloro-2-fluoropyridine (0.639 g, 4.86 mmol, 71.9% yield) as a colorless oil. Compounds 3B'-8B' were prepared by a method similar to the synthetic procedure described above for 2B'.
References
[1] Tetrahedron Letters, 2015, vol. 56, # 44, p. 6043 - 6046
[2]
Anchan, K., Baburajan, P., Puttappa, N. H., Sarkar, S. K. (2019). One-pot synthesis of substituted dibenzoxazepinones and pyridobenzoxazepinones using octacarbonyldicobalt as an effective CO source. Synthetic Communications, 50(3), 348–360.
https://doi.org/10.1080/00397911.2019.1695277
