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

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.

1. extractionextracted with ethyl acetate (3×30 mL)
2. customThe organic layer was separated
3. washwashed with 1M sodium hydroxide (3×30 mL)
4. customThe aqueous layers were separated
5. extractionre-extracted with ethyl acetate (3×30 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-892c30f659684d8ebbcebe505bfab545

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685977B2