Chloroform → Methyl 4-bromo-3-oxopentanoate
Reaction equation
[Br:1]Br.C(Cl)(Cl)Cl.[O:7]=[C:8]([CH2:14][CH3:15])[CH2:9][C:10]([O:12][CH3:13])=[O:11]>>[Br:1][CH:14]([CH3:15])[C:8](=[O:7])[CH2:9][C:10]([O:12][CH3:13])=[O:11]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
Under a nitrogen atmosphere, a solution of bromine (8.61 mL, 167 mmol) in chloroform (20 mL, 200 mmol) was added dropwise over a period of 2 h to a solution of 3-oxopentanoic acid, methyl ester (Aldrich, 21.0 mL, 167 mmol) in chloroform (147 mL, 1840 mmol), at 0° C. (ice bath). The reaction mixture was stirred for 30 min at 0° C. and then allowed to stand at room temperature overnight. While stirring, a stream of air was bubbled through the solution for 1 hour. After drying over sodium sulfate, the solvent was evaporated under reduced pressure leaving the desired compound.
Workup
- waitto stand at room temperature overnight
- stirringWhile stirring
- customa stream of air was bubbled through the solution for 1 hour
- dry with materialAfter drying over sodium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-28d6c6d4885049a6ab7d7dc854fd4ab0
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940752B2
Reaction notes
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