Hydrochloric Acid → (3-Amino-5-(trifluoromethyl)phenyl)methanol

To a solution of [3-nitro-5-(trifluoromethyl)phenyl]methanol (1.8 g, 8.0 mmol) (Step A, Example 23) in TIE (36 mL) was added concentrated HCl (18 mL) and SnCl2.2H2O (8.7 g, 38.8 mmol). The reaction was stirred at room temperature for 24 hours and then poured slowly into saturated NaHCO3 (250 mL). After neutralization was complete, the reaction was extracted with EtOAc (3×50 mL). The organic extracts were washed with brine (75 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 50% EtOAc/hexanes afforded 1.5 g (quantitative) of [3-amino-5-(trifluoromethyl)phenyl]methanol. Rf=0.35 (50% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 6.98 (s, 1H), 6.84 (s, 1H), 6.81 (s, 1H), 4.65 (s, 2H), 3.87 (bs, 1H).

1. extractionthe reaction was extracted with EtOAc (3×50 mL)
2. washThe organic extracts were washed with brine (75 mL)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customPurification by flash chromatography with 50% EtOAc/hexanes

ORD-Eintrag

ord-4c95f83a74ec44c88ac3c00fc654936e

Quelldatensatz

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08193365B2