Reacción #170941

Ecuación de reacción

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

Cyanomethylenetributylphosphorane

Tin(II) chloride dihydrate

→

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

Rendimiento 32.0%

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%) 1H 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.

Fuente