1-(DifluoroMethyl)-2-nitrobenzene synthesis

Yield:64747-65-5 86%

Reaction Conditions:

with (bis-(2-methoxyethyl)amino)sulfur trufluoride in dichloromethane at 0; for 18 h;Inert atmosphere;

Steps:

11 Example 11: Preparation of 1-(difluoromethyl)-2-nitrobenzene (C15)

To a solution of 2-nitrobenzaldehyde (1 g, 6.62 mmol) in dry DCM (33.1 mL) was added deoxofluor (4.88 mL, 13.2 mmol) in a dry 100 mL round-bottomed flask under a nitrogen atmosphere. The reaction mixture was stirred at 0 °C for 18 h. The reaction mixture was slowly poured into a solution of saturated aqueous sodium bicarbonate and stirred. The layers were separated, and the aqueous layer was extracted twice with DCM. The combined organic extracts were dried over Na₂SO₄and concentrated under vacuum. Purification by flash chromatography (silica gel) eluting with a 0-10% acetone in hexanes gradient afforded the title compound as a yellow oil (1.1 g, 86%):¹H NMR (400 MHz, CDCl₃) d 8.16 (dd, J = 8.2, 1.2 Hz, 1H), 7.91 (dd, J = 7.9, 1.4 Hz, 1H), 7.79 (td, J = 7.8, 1.4 Hz, 1H), 7.73- 7.59 (m, 1H), 7.57- 7.23 (m, 1H); EIMS m/z 173.

References:

WO2021/11722,2021,A1 Location in patent:Page/Page column 80-81