Bromine → Ethyl 2-bromo-3-oxopentanoate

HRID 577230Notes

Reaction equation

HRID 577230 reaction equation
[O:1]=[C:2]([CH2:9][CH3:10])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Br:11]Br>O>[Br:11][CH:3]([C:2](=[O:1])[CH2:9][CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 78656Ethyl 3-oxovalerate

Product 1

HCID 13048353Ethyl 2-bromo-3-oxopentanoateYield 94.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of ethyl 3-oxopentanoate (5.0 mL, 34.7 mmol) in water (30 mL) was added bromine (1.8 mL, 35.0 mmol) via syringe pump addition (0.5 h). The mixture was stirred at 0° C. for 0.5 hour. The solution was extracted with EtOAc (2×35 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording ethyl 2-bromo-3-oxopentanoate (7.3 g, 94% yield). The product was used without further purification.

Workup

  1. additionpump addition (0.5 h)
  2. extractionThe solution was extracted with EtOAc (2×35 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customdried in vacuo

Sources & evidence

ORD record
ord-bbd72309935e4ccdbe9a95a9efaa9da9
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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