تفاعل #67471

معادلة التفاعل

2-(2-Bromo-4-nitrophenyl)-2-methylpropane-1,3-diol

Cyanomethylenetributylphosphorane

Tin(II) chloride dihydrate

→

3-bromo-4-(3-methyloxetan-3-yl)aniline

المردود 32.0%

المذيبات

benzene

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture was evaporated to dryness
2. 2
   workup.DISSOLUTIONre-dissolved in 4 mL of EtOH
3. 3
   درجة الحرارةthe resulting solution was heated at 70° C. for 1 hour
4. 4
   درجة الحرارةThe mixture was cooled to room temperature
5. 5
   أخرىquenched with a saturated aqueous solution of sodium bicarbonate
6. 6
   استخلاصThe mixture was then extracted three times with ethyl acetate
7. 7
   أخرىThe combined ethyl acetate extracts were evaporated to dryness
8. 8
   أخرىpurified by preparative LC/MS

الإجراء التجريبي

2-(2-Bromo-4-nitrophenyl)-2-methylpropane-1,3-diol (0.145 g, 0.500 mmol) was dissolved in 2.5 mL of anhydrous benzene. Cyanomethylenetributylphosphorane (CMBP) (0.181 g, 0.750 mmol) was then added and the solution was allowed to stir at room temperature for 72 hours. The mixture was evaporated to dryness and then re-dissolved in 4 mL of EtOH. Tin(II) chloride dihydrate (0.564 g, 2.50 mmol) was then added and the resulting solution was heated at 70° C. for 1 hour. The mixture was cooled to room temperature and then quenched with a saturated aqueous solution of sodium bicarbonate. The mixture was then extracted three times with ethyl acetate. The combined ethyl acetate extracts were evaporated to dryness and purified by preparative LC/MS to yield 3-bromo-4-(3-methyloxetan-3-yl)aniline as a pale yellow oil (0.032 g, 32%) NMR (400 MHz, CD3CN) δ 7.13 (dd, J=0.7, 1.8 Hz, 1H), 6.94-6.88 (m, 2H), 6.75 (br s, 2H), 4.98 (d, J=5.6 Hz, 2H), 4.51 (d, J=6.1 Hz, 2H), 1.74 (s, 3H). ESI-MS m/z calc. 241.0, found; 242.1 (M+1)+ Retention time 0.53 minutes.

المصدر