Ammonium Chloride → 3-Chloro-4-(trifluoromethyl)phenol

Participants

Reaction Steps

To a solution of (2-(3-chloro-4-(trifluoromethyl)phenoxy)ethyl)trimethylsilane (Preparation 15, 3.1 g, 10 mmol) in 1,4-dioxane (5 mL) was added tetrabutylammonium fluoride (10 mL, 1M in THF) and the resulting mixture was stirred at room temperature for 18 hours under nitrogen. The mixture was poured onto water and neutralised with aq. ammonium chloride and extracted with ethyl acetate (3×30 mL). The organic layer was separated and washed with 1M sodium hydroxide (3×30 mL). The aqueous layers were separated, combined, acidified with aqueous 2M HCl and re-extracted with ethyl acetate (3×30 mL), dried (MgSO4), filtered and concentrated in vacuo to afford 2.46 g of a pale yellow oil. The crude oil was purified by silica gel column chromatography eluting with a gradient of 0-50% ethyl acetate in heptane to afford 619 mg (31%) of the title compound as a colourless oil.

Provenance & Evidence