Reacción #45339

Ecuación de reacción

H2O

t-butyl nitrite

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

dimethyl disulfide

→

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

Disolventes

CHCl3

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe mixture was extracted with EtOAc (50 mL)
2. 2
   Lavadowashed with brine (15 mL)
3. 3
   Secadodried over Na2SO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated
6. 6
   OtroPurification by flash chromatography with 0% to 50% EtOAc/hexanes

Procedimiento

To a solution of [3-amino-5-(trifluoromethyl)phenyl]methanol (319 mg, 1.67 mmol) (Step A, Example 24) in CHCl3 (5 mL) was added dimethyl disulfide (296 μL, 3.34 mmol). Next, t-butyl nitrite (285 μL, 2.4 mmol) was added dropwise by syringe. The reaction was stirred at room temperature for two hours and then poured into H2O (15 mL). The mixture was extracted with EtOAc (50 mL), washed with brine (15 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 0% to 50% EtOAc/hexanes afforded [3-(methylthio)-5-(trifluoromethyl)phenyl]-methanol. The [3-(methylthio)-5-(trifluoromethyl)phenyl]methanol was contaminated with minor impurities that were removed after the next step. Rf=0.53 (50% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 7.63 (s, 1H), 7.40 (s, 1H), 7.35 (s, 1H), 4.71 (s, 2H), 2.51 (s, 3H).

Fuente