Reacción #1929045

Ecuación de reacción

Pyridine

bromoacetyl bromide

2-phenylpropan-2-ol

→

title compound

Rendimiento 30.0%

2-phenylpropan-2-yl 2-bromoacetate

Rendimiento 30.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe reaction mixture was washed with water (3×100 mL), saturated aqueous sodium bicarbonate (3×100 mL), water (2×100 mL)
2. 2
   Secadodried (Na2SO4)
3. 3
   Concentraciónconcentrated
4. 4
   OtroThe crude residue was purified by silica gel flash column chromatography (neutralized with TEA, heptanes)

Procedimiento

Pyridine (3.84 mL, 47.7 mmol) followed by bromoacetyl bromide (4.16 mL, 47.7 mmol) was added to a solution of 2-phenylpropan-2-ol (5.00 g, 36.7 mmol) in dichloromethane (100 mL) at 0° C., warmed to r.t. and stirred overnight. The reaction mixture was washed with water (3×100 mL), saturated aqueous sodium bicarbonate (3×100 mL), water (2×100 mL), dried (Na2SO4) and concentrated. The crude residue was purified by silica gel flash column chromatography (neutralized with TEA, heptanes) to afford the title compound (2.8 g (non-optimized), 30%) as a colorless oil. 1H NMR (300 MHz, ((CD3)2CO) δ: 7.44 (d, J=7.2 Hz, 2H), 7.34 (t, J=7.2 Hz, 2H), 7.25 (t, J=7.2 Hz, 1H), 4.01 (s, 2H), 1.78 (s, 6H).

Fuente