반응 #45339

반응 방정식

H2O

t-butyl nitrite

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

dimethyl disulfide

→

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

용매

CHCl3

반응 조건

후처리

1. 1
   추출The mixture was extracted with EtOAc (50 mL)
2. 2
   세척washed with brine (15 mL)
3. 3
   건조dried over Na2SO4
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   기타Purification by flash chromatography with 0% to 50% EtOAc/hexanes

실험 절차

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).

출처