反应详情

温度

50 °C

To a solution of 8-(1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile (1.78 g, 7.11 mmol) in anhydrous DMF (25 ml) was added N-bromosuccinimide (1.52 g, 8.53 mmol). The solution was heated at 50° C. for 2 h. The reaction was cooled to 23° C. then diluted with saturated aqueous NaS2O3 (175 ml) and extracted with EtOAc (2×130 ml). The combined organic layers were washed with brine (150 ml), dried over Na2SO4, filtered and concentrated. The crude yellow oil was purified via flash column chromatography (SiO2: 100% Hex to 60:40 Hex:EtOAc), to afford 8-(5-bromo-1,3-thiazol-2-yl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile (1.43 g, 4.13 mmol, 58% yield) as an off-white solid. MS ESI: [M+H]+ m/z 331.1. 1H NMR (500 MHz, CDCl3): δ 7.66 (s, 1H), 4.01-3.93 (m, 4H), 2.39-2.26 (m, 4H), 2.07-2.01 (m, 2H), 1.88-1.86 (m, 2H).

1. temperatureThe reaction was cooled to 23° C.
2. extractionextracted with EtOAc (2×130 ml)
3. washThe combined organic layers were washed with brine (150 ml)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude yellow oil was purified via flash column chromatography (SiO2: 100% Hex to 60:40 Hex:EtOAc)