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

HRID 2251860ノート

反応式

HRID 2251860 の反応式
[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]

参加物

5

反応物 3

HCID 12651086Methyl 2-(chlorocarbonyl)-6-nitrobenzoateHCID 178418546HCID 178418546、化合物HCID 178418573HCID 178418573、化合物

生成物 1

HCID 59644399Methyl 2-acetyl-6-nitrobenzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-673a74252478423db9562632fdee041b
出典データセット
uspto-grants-2008_01
特許番号
US07320992B2

反応ノート

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