Ethyl bromoacetate → HCID 86629740, compound

HRID 2426245Notes

Reaction equation

HRID 2426245 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([N+:16]([O-:18])=[O:17])[C:5]([CH:11]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:12]([O:14][CH3:15])=[O:13])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 57457660HCID 57457660, compound

Product 1

HCID 86629740HCID 86629740, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl (4-fluoro-2,6-dinitrophenyl)acetate from Step B (9.51 g, 36.8 mmol) and ethyl bromoacetate (8.17 mL, 73.6 mmol) in DMF (100 mL) was added cesium carbonate (18.0 g, 55.2 mmol). The reaction mixture was stirred for 16 h and then poured onto H2O (500 mL). The aqueous layer was extracted with EtOAc (3×250 mL). The combined organic layers were washed with H2O (100 mL), dried over Na2SO4, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexanes:EtOAc—100:0 to 80:20, to give the title compound. MS: m/z=345 (M+1).

Workup

  1. additionpoured onto H2O (500 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (3×250 mL)
  3. washThe combined organic layers were washed with H2O (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexanes

Sources & evidence

ORD record
ord-7007c5e116994c8ebff5a247d166a489
Source dataset
uspto-grants-2011_06
Patent number
US07968540B2

Reaction notes

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