반응 #1929045

반응 방정식

Pyridine

bromoacetyl bromide

2-phenylpropan-2-ol

→

title compound

수율 30.0%

2-phenylpropan-2-yl 2-bromoacetate

수율 30.0%

용매

dichloromethane

반응 조건

후처리

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

실험 절차

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).

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