Bromine → Ethyl 2-bromo-4-methyl-3-oxopentanoate
Reaction equation
[CH3:1][CH:2]([CH3:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:12]Br>O>[Br:12][CH:4]([C:3](=[O:10])[CH:2]([CH3:1])[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a 0° C. solution of ethyl 4-methyl-3-oxopentanoate (5.0 mL, 31 mmol) in water (20 mL) was added bromine (16 mL, 31.3 mmol) via syringe pump (0.5 hour). The mixture was stirred at 0° C. for 0.5 hour. The solution was extracted with EtOAc (3×20 mL). The organic extracts were combined, extracted with brine (2×60 mL), dried over MgSO4, filtered, evaporated, and dried in vacuo, affording ethyl 2-bromo-4-methyl-3-oxopentanoate (6.0 g, 82% yield). The product was used without further purification.
Workup
- extractionThe solution was extracted with EtOAc (3×20 mL)
- extractionextracted with brine (2×60 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
- customdried in vacuo
Sources & evidence
- ORD record
- ord-381103fa9ebc477988084d53a0aff1b4
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315521B2
Reaction notes
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