ChemicalBook CAS DataBase List 4-(Bromomethyl)-5-hydrofuran-2-one

4-(Bromomethyl)-5-hydrofuran-2-one synthesis

6synthesis methods

Product Name:4-(Bromomethyl)-5-hydrofuran-2-one
CAS Number:61934-55-2
Molecular formula:C5H5BrO2
Molecular Weight:177

75887-43-3

61934-55-2

Synthesis of 4-(bromomethyl)furan-2(5H)-one (8): 5% aqueous sodium hydroxide solution (100 mL) was stirred with compound 7 (1.98 g, 7.68 mmol) at room temperature overnight. After completion of the reaction, the reaction mixture was extracted with dichloromethane (3 x 150 mL), the organic phase was washed sequentially with saturated aqueous sodium bicarbonate solution and distilled water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography (eluent ratio 4:1 hexane:ethyl acetate) afforded the target product 8 as a mixture of enol-keto interconverting isomers in the form of a yellow oil (150 mg, 11% yield). Thin layer chromatography (TLC) showed an Rf value of 0.00 (eluent ratio 4:1 hexane:ethyl acetate). The NMR hydrogen spectra (500 MHz, CDCl3) δH of the ketone interconversion isomers: 4.24 (2H, single peak, CH2Br), 4.98 (2H, single peak, CH2), 6.16 (1H, single peak, CH). NMR carbon spectrum (125.77 MHz, CDCl3) δC: 41.33 (CH2Br), 74.05 (CH2), 121.09 (CH), 155.42 (C), 178.32 (C=O). NMR hydrogen spectrum (500 MHz, CDCl3) δH of the enol intercalation isomers: 2.30 (1H, multiple peaks, CH2CH), 4.20 (2H, multiple peaks, CH2Br), 4.74 (2H, multiple peaks, CH2), 6.09 (1H, single peaks, CH), 9.10 (1H, broad single peaks, OH). Mass spectra (EI): m/z 149 [M-CO]- (100%), 96 (40), 68 (50), 39 (70). Gas Chromatography (GC) retention time: 6.57 min.

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61934-55-2
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Yield:61934-55-2 89%

Reaction Conditions:

with sodium hydroxide in water at 20; for 12 h;

References:

Crotti, Antonio E. M.;Bronze-Uhle, Erika S.;Nascimento, Paulo G. B. D.;Donate, Paulo M.;Galembeck, Sergio E.;Vessecchi, Ricardo;Lopes, Norberto P. [Journal of Mass Spectrometry,2009,vol. 44,# 12,p. 1733 - 1741] Location in patent:experimental part