Reaktion #45334

Reaktionsgleichung

NaHCO3

[3-nitro-5-(trifluoromethyl)phenyl]methanol

HCl

SnCl2.2H2O

→

[3-amino-5-(trifluoromethyl)phenyl]methanol

Ausbeute 98.1%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe reaction was extracted with EtOAc (3×50 mL)
2. 2
   WaschenThe organic extracts were washed with brine (75 mL)
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigePurification by flash chromatography with 50% EtOAc/hexanes

Vorschrift

To a solution of [3-nitro-5-(trifluoromethyl)phenyl]methanol (1.8 g, 8.0 mmol) (Step A, Example 23) in THF (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).

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