Chemical Properties
CLEAR YELLOW LIQUID
Uses
2,5-Difluoronitrobenzene was used in the synthesis of :
- N-alkylated 2-arylaminobenzimidazoles
- quinoxalinones
- N-(2-nitro-4-fluorophenyl)-l,2,3,4-tetrahydroisoquinoline
Synthesis
GENERAL STEPS: In a FEP or PFA reactor fitted with a PTFE-lined magnetic stir bar and connected to a gas scrubber bottle, substituted benzene (0.95-1.10 mmol), 1,1,1,3,3-pentafluorobutane (2 mL per mL of C6H5R), and BF3-Et2O (1.3-1.5 mmol/mmol C6H5R) were added. The mixture was stirred at 0-5 °C (ice bath) for 10-15 min, followed by batchwise addition of XeF2 (1.2-1.3 mmol/mmol C6H5R). After each addition, the mixture was stirred at 22-25 °C for 3-5 min and recooled. After the addition was completed, the dark solution was continued to be stirred at 22-25 °C for 15-30 min. At the end of the reaction, the reaction was quenched by the addition of 10% aqueous KHCO3, the upper organic layer was separated and filtered through a short column packed with silica gel (40-60 μm) and subsequently dried with magnesium sulfate. The final products were analyzed by 19F NMR and GC/MS. The major products are listed in the table and the others are as follows (with GC/MS data).
References
[1] Russian Journal of Organic Chemistry, 2016, vol. 52, # 10, p. 1400 - 1407
[2] Zh. Org. Khim., 2016, vol. 52, # 10, p. 1412 - 1419,8
