Benzyl 2-bromoacetate synthesis
- Product Name:Benzyl 2-bromoacetate
- CAS Number:5437-45-6
- Molecular formula:C9H9BrO2
- Molecular Weight:229.07
Yield:5437-45-6 100%
Reaction Conditions:
with toluene-4-sulfonic acid in benzene at 120; for 24 h;
Steps:
1
[First Step]: Bromoacetic acid (20.8 g, 150 mmol), benzyl alcohol (16.2 g, 150 mmol), p-toluenesulfonic acid (258 mg, 1.5 mmol) and benzene (300 mL) were added to a two-necked flask equipped with a Dean-Stark trap, and were subjected to dehydration condensation at 120°C for 24 hours, and then the solvent was distilled off under reduced pressure with an evaporator. Then, the residue was purified by silica gel flash column chromatography (hexane/ethyl acetate=10/1, 5/1), and thus bromoacetic acid benzyl ester (34.3 g, 150 mmol) was obtained quantitatively as a yellow oily product. Rf 0.71 (hexane/ethyl acetate=4/1); 1H NMR (500 MHz, ppm, CDCl3, J=Hz) δ 3.81 (s, 2H), 5.14 (s, 2H), 7.31 (s, 5H); 13C NMR (125 MHz, ppm, CDCl3) δ 25.74, 67.79, 128.27, 128.48, 128.54, 134.88, 166.91; IR (neat, cm-1) 2959, 1751, 1458, 1412, 1377, 1167, 972, 750, 698
References:
Sumitomo Chemical Company, Limited;National University Corporation Tottori University EP2345651, 2011, A1 Location in patent:Page/Page column 11
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