反応 #1929045

反応方程式

Pyridine

bromoacetyl bromide

2-phenylpropan-2-ol

→

title compound

収率 30.0%

2-phenylpropan-2-yl 2-bromoacetate

収率 30.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   洗浄The reaction mixture was washed with water (3×100 mL), saturated aqueous sodium bicarbonate (3×100 mL), water (2×100 mL)
2. 2
   乾燥dried (Na2SO4)
3. 3
   濃縮concentrated
4. 4
   その他The crude residue was purified by silica gel flash column chromatography (neutralized with TEA, heptanes)

実験手順

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).

出典