Ethyl 2-bromo-3-(4-methoxyphenyl)-3-oxopropanoate → HCID 59587379, compound

HRID 389698Notes

Reaction equation

HRID 389698 reaction equation
Br[CH:2]([C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:20]=1[C:21]([O-:23])=[O:22].[Na+]>C(O)C.CCOC(C)=O.O>[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:20]=1[C:21]([O:23][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:9])=[O:22]

Participants

6

Reactant 2

HCID 13048360Ethyl 2-bromo-3-(4-methoxyphenyl)-3-oxopropanoateHCID 23698872Sodium 2,6-difluorobenzoate

Product 1

HCID 59587379HCID 59587379, compoundYield 96.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 2-bromo-3-(4-methoxyphenyl)-3-oxopropanoate (0.090 g, 0.3 mmol) and sodium 2,6-difluorobenzoate (0.054 g, 0.30 mmol) in ethanol (2 mL) was heated at 120° C. in the microwave for 10 minutes. The reaction mixture was diluted with EtOAc (25 mL) and water (25 mL). The organic phase was washed with water and brine, dried over MgSO4 and the solvent evaporated in vacuo. The residue was purified by silica gel column chromatography using a gradient of 0-40% EtOAc in hexanes to afford 3-ethoxy-1-(4-methoxyphenyl)-1,3-dioxopropan-2-yl 2,6-difluorobenzoate (0.108 g, 0.29 mmol, 96%) as a clear film. 1H NMR (CDCl3) δ 1.27 (3H, t), 3.89 (3H, s), 4.30 (2H, m), 6.47 (1H, s), 6.97 (4H, m), 7.46 (1H, m), 8.06 (2H, d). LCMS (1) Rt: 2.26 min; m/z (ES+) 379.

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried over MgSO4
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-be4053e71b4a4939b2a17ea4c33a982b
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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