Reacción #1973909

Ecuación de reacción

Ethyl 2-oxocyclohexanecarboxylate

Bromine

→

3-Bromo-2-hydroxy-1-enecarboxylic

Rendimiento 94.4%

3-Bromo-2-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

Rendimiento 94.4%

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to RT over 90 min
2. 2
   Extracciónextracted with ethyl acetate (3×200 mL)
3. 3
   SecadoThe combined organic layers were dried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   Otrodried on the vacuum line for 18 h

Procedimiento

Ethyl 2-oxocyclohexanecarboxylate (30 g, 176 mmol, 28 mL) was dissolved in diethyl ether (30 mL) and cooled to 0° C. under nitrogen. Bromine (28 g, 176 mmol, 9.0 mL) was added dropwise over 15 min and the reaction mixture was allowed to warm to RT over 90 min. The mixture was slowly poured into ice-cold saturated aqueous potassium carbonate (250 mL) and extracted with ethyl acetate (3×200 mL). The combined organic layers were dried over magnesium sulfate, filtered, concentrated in vacuo and dried on the vacuum line for 18 h to afford 41.4 g (94%) of 3-Bromo-2-hydroxy-1-enecarboxylic acid ethyl ester (4) as a yellow oil. The structure was confirmed by 13C NMR (75 MHz, CDCl3): δC 14.1, 17.7, 21.8, 32.0, 60.0, 60.8, 99.7, 166.3, and 172.8.

Fuente