Water → Ethyl 2-bromo-3-oxobutanoate

HRID 560289Notes

Reaction equation

HRID 560289 reaction equation
FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16].[Br:22]Br.O>C(Cl)Cl>[CH2:20]([O:19][C:13](=[O:18])[CH:14]([Br:22])[C:15](=[O:16])[CH3:17])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8868Ethyl AcetoacetateHCID 24408BromineHCID 65367Trimethylsilyl triflate

Product 1

HCID 11206579Ethyl 2-bromo-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

At −5° C. trimethylsilyl trifluoromethanesulfonate (36.9 mmol) is added dropwise to a solution of ethyl acetoacetate (30.7 mmol) and TEA (36.9 mmol) in DCM (50 mL). The solution is stirred for 90 min at 0° C. and treated over 30 min with a solution of bromine (30.7 mmol) in DCM (20 mL). After 60 min water (100 mL) is added, the layers are separated and the aq. layer is extracted three times with water (100 mL each). The organic layer is dried over MgSO4 and concentrated under reduced pressure to give the desired product which is used without further purification. 1H-NMR (CDCl3): δ=1.34 (t, J=7.16 Hz, 3H); 2.46 (s, 3H); 4.31 (q, J=7.20 Hz, 2H); 4.77 (s, 1H).

Workup

  1. customthe layers are separated
  2. extractionthe aq. layer is extracted three times with water (100 mL each)
  3. dry with materialThe organic layer is dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45d0d9ec12c74e36bdd88efc7ec51e2f
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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