Bromine → 3-Bromo-2-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester
Reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[Br:13]Br>C(OCC)C>[CH2:11]([O:10][C:8]([C:3]1[CH2:4][CH2:5][CH2:6][CH:7]([Br:13])[C:2]=1[OH:1])=[O:9])[CH3:12]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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.
Workup
- temperatureto warm to RT over 90 min
- extractionextracted with ethyl acetate (3×200 mL)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customdried on the vacuum line for 18 h
Sources & evidence
- ORD record
- ord-4dc2542805af4de4a88a1f62e8f79b3c
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09168317B2
Reaction notes
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