Bromine → Ethyl 3-bromo-6-chloro-2-oxohexanoate

HRID 1518268Notes

Reaction equation

HRID 1518268 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Br:13]Br>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O>[Br:13][CH:5]([CH2:4][CH2:3][CH2:2][Cl:1])[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 24408BromineHCID 12252847Ethyl 6-chloro-2-oxohexanoate

Product 1

HCID 59418695Ethyl 3-bromo-6-chloro-2-oxohexanoate

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To ethyl 6-chloro-2-oxohexanoate (2.9 g, 15 mmol) in carbon tetrachloride (30 mL) was added bromine (0.85 mL, 16.5 mmol) and stirred at rt for 1 hour. The reaction mixture was diluted with EtOAc, washed with Na2S2O3 solution, water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with a gradient of 0 to 10% EtOAc in hexanes to provide the desired product ethyl 3-bromo-6-chloro-2-oxohexanoate (2A) in 95% yield. 1H NMR (300 MHz, DMSO-d6) δ ppm 5.25 (1H, dd), 4.29 (2H, q), 3.71 (2H, t), 2.16 (1H, m), 1.91 (1H, m), 1.29 (3H, t).

Workup

  1. washwashed with Na2S2O3 solution, water, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by column chromatography on silica gel eluting with a gradient of 0 to 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-01b6aa281f6144d18f3bdc7e5e9bae1f
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

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