Hydrochloric Acid → (2-Amino-5-(trifluoromethoxy)phenyl)methanol

A solution of tert-butyl 2-(hydroxymethyl)-4-(trifluoromethoxy)phenylcarbamate (19.3 g, 62.9 mmol) in dioxane (100 mL) was treated with a 4 N solution of HCl in dioxane (126 mL, 504 mmol HCl), and the mixture was stirred overnight. The solution was concentrated in-vacuo, the residue was partitioned between ethyl acetate (200 mL) and saturated sodium bicarbonate (200 mL), and the mixture was stirred until gas evolution had ceased. The layers were separated, the organic phase was washed with saturated sodium bicarbonate (100 mL), water (100 mL), brine (100 mL), dried over sodium sulfate, and concentrated in-vacuo to yield 12.3 g of a pale yellow oil, which was used as-is in the next step. 1H NMR (400 MHz, DMSO) δ ppm 4.36 (m, 2 H) 5.14 (m, 3 H) 6.64 (d, J=8.79 Hz3, 1 H) 6.92 (dd, J=8.79, 2.64 Hz, 1 H) 7.06 (s, 1 H).

1. concentrationThe solution was concentrated in-vacuo
2. customthe residue was partitioned between ethyl acetate (200 mL) and saturated sodium bicarbonate (200 mL)
3. stirringthe mixture was stirred until gas evolution
4. customThe layers were separated
5. washthe organic phase was washed with saturated sodium bicarbonate (100 mL), water (100 mL), brine (100 mL)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in-vacuo

ORD record

ord-eef2873f3c3b4ecca8c61b8e0fac3d22

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696205B2