2-(2-Bromoethyl)-1,3-dioxolane synthesis
- Product Name:2-(2-Bromoethyl)-1,3-dioxolane
- CAS Number:18742-02-4
- Molecular formula:C5H9BrO2
- Molecular Weight:181.03
107-21-1
1302 suppliers
$10.00/25g
107-02-8
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$38.60/4s8501
18742-02-4
290 suppliers
$6.00/5g
Yield:18742-02-4 82%
Reaction Conditions:
with hydrogen bromide in 1,4-dioxane at 5 - 20; for 0.5 h;
Steps:
Typical procedure for the preparation of 2-(2-bromoalkyl)-1,3-dioxolanes with HBr/1,4-dioxane (1c)
To a mixture of acrolein (90%, 374 mg, 6.0 mmol), ethylene glycol(460 mg, 7.4 mmol) in 1,4-dioxane (5 mL), 1c (17%, 4.0 g,8.4 mmol) was added at 5 C. The mixture was then warmed to room temperature for 30 min with stirring. The resulting mixture was quenched with saturated aq. NaHCO3 (20 mL) and extracted with diethyl ether (15 mL 3). The combined organic layer was washed with brine (25 mL 3), dried over Na2SO4 (10 g) and concentrated in vacuo. The crude residue was purified by column chromatography on florisil (eluent: pentane) to afford 10a (890 mg, 82%) as a colourless liquid. 1H NMR (500 MHz, CDCl3) δ 2.22 (dt, J = 4.6 Hz, J = 7.4 Hz, 2H), 3.47 (t, J = 7.1 Hz, 2H), 3.88 (m,2H), 3.96 (m, 2H), 5.01 (t, J = 4.6 Hz, 1H); 13C NMR (126 MHz,CDCl3) δ 27.14, 36.97, 64.78 (2C), 102.34.
References:
Nishio, Yuya;Mifune, Ryota;Sato, Taisuke;Ishikawa, Shin-ich;Matsubara, Hiroshi [Tetrahedron Letters,2017,vol. 58,# 12,p. 1190 - 1193]
3984-22-3
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$146.00/5ml
18742-02-4
290 suppliers
$6.00/5g