Bromine → Methyl 4-bromo-3-oxohexanoate
Reaction equation
[Br:1]Br.[O:3]=[C:4]([CH2:10][CH2:11][CH3:12])[CH2:5][C:6]([O:8][CH3:9])=[O:7]>C(Cl)(Cl)Cl>[Br:1][CH:10]([CH2:11][CH3:12])[C:4](=[O:3])[CH2:5][C:6]([O:8][CH3:9])=[O:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Under a nitrogen atmosphere, a solution of bromine (8.61 mL, 167 mmol) in chloroform (20 mL) was added drop-wise over a period of 2 h to a solution of methyl 3-oxohexanoate (Fluka, 24.1 g, 167 mmol) in chloroform (147 mL), at 0° C. (ice bath). The reaction mixture was stirred for 30 min at 0° C. and then allowed to warm to room temperature overnight. While stirring, a stream of air was bubbled through the solution for 1 hour. The reaction mixture was dried over sodium sulfate and the solvent evaporated under reduced pressure to provide the desired compound.