Sodium Iodide → 2-Nitro-6-(2-oxoethyl)benzoic Acid Methyl Ester

HRID 133109Notes

Reaction equation

HRID 133109 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:13]=[CH:14][O:15]C.[Na+].[I-].C[Si](Cl)(C)C>CC#N>[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:5]([CH2:13][CH:14]=[O:15])=[CH:6][CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 674228532-(2-Methoxyvinyl)-6-nitrobenzoic Acid Methyl Ester

Product 1

HCID 866906922-Nitro-6-(2-oxoethyl)benzoic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(2-methoxy-vinyl)-6-nitro-benzoic acid methyl ester (Step A, 3.33 g, 14.1 mmol, 1.0 eq) and CH3CN (20 mL) was added NaI (2.3 g, 15.5 mmol, 1.1 eq) and TMSCl (2 mL, 15.5 mmol, 1.1 eq). The reaction was stirred at RT for 4 h, then quenched with saturated NH4Cl and extracted with EtOAc. The organic layer was washed with H2O and brine, dried (MgSO4) and concentrated in vacuo to give a red-orange oil. Purification by silica flash chromatography (0-30% EtOAc:hexane) gave the desired compound as an orange oil.

Workup

  1. customquenched with saturated NH4Cl
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a red-orange oil
  7. customPurification by silica flash chromatography (0-30% EtOAc:hexane)

Sources & evidence

ORD record
ord-dcb414ecfee04c93870763d0454e2051
Source dataset
uspto-grants-2008_06
Patent number
US07390820B2

Reaction notes

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