Reaction #86512

Reaction equation

bromine

chloroform

3-oxopentanoic acid, methyl ester

chloroform

→

desired compound

methyl 4-bromo-3-oxopentanoate

Conditions

Workup

1. 1
   workup.WAITto stand at room temperature overnight
2. 2
   workup.STIRRINGWhile stirring
3. 3
   Othera stream of air was bubbled through the solution for 1 hour
4. 4
   DryingAfter drying over sodium sulfate
5. 5
   Otherthe solvent was evaporated under reduced pressure

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.

Source