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ChemicalBook CAS DataBase List 2(5H)-FURANONE,4-BROMO-5-ETHOXY-
32978-38-4

2(5H)-FURANONE,4-BROMO-5-ETHOXY- synthesis

2synthesis methods
-

Yield: 82%

Reaction Conditions:

with bromine in tetrachloromethane at 0 - 20; for 3.5 h;

Steps:

1
Example 1; Preparation of 4-bromo-5-ethoxy-5H-furan-2-one [0128]; This procedure may be carried out in a manner similar to that described by C. Escobar, et al., Ann. Quim. (1971), 67,43- 57. ). To a solution of 5-ethoxy-5H-furan-2-one (II, R1=Et) (10.0 g, 78.0 mmol) in carbon tetrachloride (50 mL) at 0°C is added over 0. 5h a solution of bromine (4.05 mL, 78.2 mmol) in carbon tetrachloride (25 mL). The reaction is stirred lh at 0°C, then 2h at room temperature. The solvents are removed under reduced pressure and the residue was short-path distilled at pump vacuum (about 0.5mm). The fraction collected at 100°C-120°C provided 4-bromo-5-ethoxy-5H-furan-2-one (13.2 g, 82% yield) as a yellow oil. 1H-NMR (500 MHz, CDC13) 8 6.24 (s, 1H), 5.63 (s, 1H), 3.71 (m, 1H), 3. 63 (m, 1H), 1.14 (t, J=7. 1Hz, 3H) ppm.

References:

VERTEX PHARMACEUTICALS INCORPORATED? WO2005/90334, 2005, A2 Location in patent:Page/Page column 66-67