Chlorodifluoromethane → 1-Bromo-3-(difluoromethoxy)-5-fluorobenzene

Participants

Reaction Steps

A mixture of 3-bromo-5-fluorophenol. (6.1 g, 31.0 mmol; see step (ii) above) and chlorodifluoromethane (13.0 g, 150.0 mmol) in i-PrOH (100 mL) and 30% KOH (80 mL) was heated in a sealed flask for 18 h at 80–85° C. The reaction mixture was cooled to room temperature and the layers were separated. The organic layer was concentrated in vacuo to afford a colourless oil. The aqueous layer was extracted with Et2O (3×30 mL). The crude oil and the combined organic extracts were washed with 2N NaOH (3×30 mL) and H2O (3×30 mL). The organics were then dried (Na2SO4), filtered through a small silica gel plug, and concentrated in vacuo to afford the sub-title compound (6.1 g, 79%) as a colourless oil that was used without further purification.

Provenance & Evidence