Reaction #1929045

Reaction equation

Pyridine

bromoacetyl bromide

2-phenylpropan-2-ol

→

title compound

Yield 30.0%

2-phenylpropan-2-yl 2-bromoacetate

Yield 30.0%

Solvents

dichloromethane

Conditions

Workup

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

Procedure

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).

Source