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

HRID 2178227Notes

Reaction equation

HRID 2178227 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

Ethyl 6-chloro-2-oxohexanoate (2.9 g, 15 mmol) in carbon tetrachloride (30 mL) was treated with bromine (0.85 mL, 16.5 mmol) and stirred at ambient temperature for 1 hour. The reaction mixture was diluted with EtOAc, washed with Na2S2O3 solution, water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The concentrate was purified by column chromatography on silica gel eluting with a gradient of 0 to 10% EtOAc in hexanes to provide (95%) of the desired product ethyl 3-bromo-6-chloro-2-oxohexanoate (23A) as a pale yellow oil: 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 and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was purified by column chromatography on silica gel eluting with a gradient of 0 to 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-0aefa5dcfdad43b389feb454020716b8
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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