Reaction #86500

Reaction equation

bromine

methyl 3-oxohexanoate

→

desired compound

methyl 4-bromo-3-oxohexanoate

Solvents

chloroform

chloroform

Conditions

Workup

1. 1
   Otherat 0° C.
2. 2
   Temperatureto warm to room temperature overnight
3. 3
   workup.STIRRINGWhile stirring
4. 4
   Othera stream of air was bubbled through the solution for 1 hour
5. 5
   DryingThe reaction mixture was dried over sodium sulfate
6. 6
   Otherthe solvent evaporated under reduced pressure

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.

Source