تفاعل #45339

معادلة التفاعل

H2O

t-butyl nitrite

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

dimethyl disulfide

→

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

المذيبات

CHCl3

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe mixture was extracted with EtOAc (50 mL)
2. 2
   غسيلwashed with brine (15 mL)
3. 3
   تجفيفdried over Na2SO4
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated
6. 6
   أخرىPurification by flash chromatography with 0% to 50% EtOAc/hexanes

الإجراء التجريبي

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).

المصدر