Potassium Carbonate → Methyl 2-bromo-3-(4-fluorophenyl)-3-oxopropanoate

HRID 1186701Notes

Reaction equation

HRID 1186701 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[Br:15]Br.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Br:15][CH:9]([C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:14])[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24408BromineHCID 579425Methyl 4-fluorobenzoylacetate

Product 1

HCID 24745534Methyl 2-bromo-3-(4-fluorophenyl)-3-oxopropanoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 3-(4-fluorophenyl)-3-oxopropanoate 76 (1 equiv, 500 mg, 2.55 mmol) in DCM (17 mL) was added a solution of bromine (1.3 equiv, 530 mg, 3.31 mmol) in DCM (1.5 mL) in a drop wise manner at 0° C. The reaction mixture was stirred further for an additional 1 h and then treated with 10% aqueous K2CO3 (5 mL) solution. The organic phase was separated, dried over Na2SO4, filtered and concentrated under reduced pressure to afford methyl 2-bromo-3-(4-fluorophenyl)-3-oxopropanoate 78 (700 mg, 100% yield). LRMS (ESI): (calc) 273.96 (found) 275.108 (MH+)+.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-692835dda4e2408889d94cef4596c211
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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