Benzyl 2-bromoacetate synthesis
- Product Name:Benzyl 2-bromoacetate
- CAS Number:5437-45-6
- Molecular formula:C9H9BrO2
- Molecular Weight:229.07
79-08-3
100-51-6
103-50-4
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General method: A mixture of acid 2 (0.033 g), 2-bromoacetic acid (3a) (0.137 g, 0.988 mmol) adsorbed on silica gel and benzyl alcohol (4a) (0.108 g, 1.000 mmol) was stirred and reacted at 80°C for 24 h under argon protection. After completion of the reaction, the mixture was cooled to room temperature, ether (5 mL x 5) was added for extraction, and the organic layer was separated by decantation from the silica gel adsorbed acid 2. The organic layer was concentrated under reduced pressure to remove the solvent, and then purified by silica gel column chromatography to afford benzyl 2-bromoacetate (5aa) (0.189 g, 83% yield) using hexane/ethyl acetate (v/v = 10/1) as eluent. The silica gel adsorbed acid 2 was recovered by vacuum drying at room temperature to give a white powder (0.033 g, 99% recovery).
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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