Methyl 2-(chlorocarbonyl)-6-nitrobenzoate → Methyl 2-acetyl-6-nitrobenzoate

HRID 2251860Notes

Reaction equation

HRID 2251860 reaction equation
[Cu][C:2]#N.C[Mg]Br.[CH3:7][O:8][C:9](=[O:22])[C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:11]=1[C:19](Cl)=[O:20]>C1COCC1>[CH3:7][O:8][C:9](=[O:22])[C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[CH:12][C:11]=1[C:19](=[O:20])[CH3:2]

Participants

5

Reactant 3

HCID 12651086Methyl 2-(chlorocarbonyl)-6-nitrobenzoateHCID 178418546HCID 178418546, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59644399Methyl 2-acetyl-6-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a suspension of copper(I)cyanide (5.70 g, 63.6 mmol) in 200 mL of anhydrous THF at −78° C. was added methyl magnesium bromide (1.4 M in toluene and THF, 43 mL, 59.3 mmol). The mixture was stirred at −20° C. for 20 min, then cooled to −78° C. A solution of 2-chlorocarbonyl-6-nitro-benzoic acid methyl ester (11.6 g, 47.8 mmol, Step B) in 30 mL of THF was added. The mixture was cooled at −10° C., and slowly warmed to RT, quenched with NH4Cl(aq), and extracted with EtOAc. The combined organic portions were washed with brine, dried over MgSO4, filtered, condensed, and purified by flash column chromatography, to provide the titled compound as a white solid.

Workup

  1. temperaturecooled to −78° C
  2. temperatureThe mixture was cooled at −10° C.
  3. temperatureslowly warmed to RT
  4. customquenched with NH4Cl(aq)
  5. extractionextracted with EtOAc
  6. washThe combined organic portions were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customcondensed
  10. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-673a74252478423db9562632fdee041b
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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