Synthesis
General procedure: A flame-dried solution of m-bromobenzaldehyde (1.0 eq.) dissolved in dichloromethane (DCM, 1.0 M) was added to a flame-dried flask at room temperature, followed by the addition of ethanol (EtOH, 5-100 μL) and diethylaminosulfur trifluoride (DAST, 1.7 eq.). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction was quenched with saturated aqueous sodium bicarbonate (NaHCO3) and extracted with dichloromethane (DCM). The organic phases were combined, washed with brine, dried over anhydrous magnesium sulfate (MgSO4) and concentrated to dryness. Finally, the product was purified by silica gel column chromatography to afford the target compound 3-difluoromethylbromobenzene.
References
[1] Synlett, 2016, vol. 27, # 1, p. 25 - 28
[2] Patent: WO2015/171610, 2015, A2. Location in patent: Paragraph 000525
[3] Journal of the American Chemical Society, 1971, vol. 93, # 19, p. 4715 - 4724
[4] Patent: US6344558, 2002, B1. Location in patent: Example 9
[5] Patent: WO2018/115380, 2018, A1. Location in patent: Page/Page column 96
