Bromine → Ethyl 4-bromo-3-oxopentanoate

HRID 1501780Notes

Reaction equation

HRID 1501780 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>C(Cl)(Cl)Cl>[Br:11][CH:9]([CH3:10])[C:2](=[O:1])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 78656Ethyl 3-oxovalerate

Product 1

HCID 12780443Ethyl 4-bromo-3-oxopentanoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of ethyl 3-oxopentanoate (5.00 g, 34.7 mmol) in chloroform (27 mL) at 0° C. was added bromine (1.79 mL, 34.7 mmol) in chloroform (10 mL) drop-wise. The resulting solution was stirred at rt for 16 h. The solution was washed with water, dried over sodium sulfate, concentrated to give ethyl 4-bromo-3-oxopentanoate. 1HNMR (500 MHz, CDCl3), δ4.670-4.630 (dd, J=6.7 Hz, 1H), 4.251-4.208(dd, J=7.2 Hz, 2H), 3.883-3.851(d, J=16 Hz, 1H), 3.687-3.655(d, J=16 Hz, 1H), 1.804-1.791 (d, J=6.8 Hz, 3H), 1.323-1.295 (m, J=7.2 Hz, 3H).

Workup

  1. washThe solution was washed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1cb2bc56aa204001b52cca01a852225e
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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