Reacción #478604

Ecuación de reacción

thionyl bromide

(S)-1-(3-bromo-5-(trifluoromethyl)phenyl)ethanol

thionyl bromide

→

(S)-1-Bromo-3-(1-bromoethyl)-5-(trifluoromethyl)benzene

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe ice bath was removed
2. 2
   TemperaturaThe reaction was warmed
3. 3
   Temperaturato reflux
4. 4
   workup.WAITheld there for 1 h
5. 5
   Temperaturaat reflux for 2 h
6. 6
   Otroquenched by addition of water
7. 7
   workup.ADDITIONdiluted with pentane
8. 8
   LavadoThe organics were washed with water (2×)
9. 9
   Secadobrine, dried over magnesium sulfate
10. 10
    Concentraciónconcentrated
11. 11
    OtroColumn chromatography (100% hexanes) gave 78 mg (42%)

Procedimiento

To a solution of (S)-1-(3-bromo-5-(trifluoromethyl)phenyl)ethanol (150 mg, 0.56 mmol) in dichloromethane (3 mL) at 0° C. was added thionyl bromide (0.086 mL, 1.12 mmol). The ice bath was removed and stirring continued for 1 h. The reaction was warmed to reflux and held there for 1 h. The reaction was treated with a second portion of thionyl bromide (0.086 mL, 1.12 mmol) and the reaction held at reflux for 2 h. The reaction was cooled to 0° C., quenched by addition of water, and diluted with pentane. The organics were washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (100% hexanes) gave 78 mg (42%). 1H NMR (500 MHz, CDCl3) δ ppm 7.76 (s, 1H), 7.68 (s, 1H), 7.60 (s, 1H), 5.12 (q, J=7.0 Hz, 1H), 2.03 (d, J=7.0 Hz, 3H); 13C NMR (126 MHz, CDCl3) δ ppm 146.4, 133.5, 132.9 (q, J=32.6 Hz), 128.4 (q, J=3.8 Hz), 123.0, 123.0 (q, J=273 Hz), 122.6 (q, J=3.8 Hz), 46.1, 26.6.

Fuente