Synthesis
General procedure for the synthesis of 2-bromo-4'-fluoroacetophenone using 4-fluoroacetophenone as starting material: general method: oxone (1.352 g, 2.2 mmol) was added to a well-stirred methanol (10 ml) solution of 4-fluoroacetophenone (2 mmol) and NH4Br (0.215 g, 2.2 mmol), and the reaction mixture was stirred at room temperature (or refluxed at temperature reaction). The reaction progress was monitored by TLC. Upon completion of the reaction, the reaction mixture was quenched with aqueous sodium thiosulfate, followed by extraction with ethyl acetate (3 x 25 ml). The organic layers were combined, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to remove the solvent to give the crude product. The crude product was further purified by silica gel column chromatography (200-300 mesh) to give pure 2-bromo-4'-fluoroacetophenone. All products were structurally confirmed by 1H NMR and mass spectrometry data.
References
[1] Farmaco, 1993, vol. 48, # 6, p. 857 - 869
[2] Synthesis, 2008, # 2, p. 253 - 266
[3] Tetrahedron Letters, 2012, vol. 53, # 2, p. 191 - 195
[4] Tetrahedron, 1992, vol. 48, # 1, p. 67 - 78
[5] Bulletin of the Chemical Society of Japan, 1999, vol. 72, # 6, p. 1327 - 1334
