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

HRID 2251860노트

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HRID 2251860 반응식
[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]

참가 물질

5

반응물 3

HCID 12651086Methyl 2-(chlorocarbonyl)-6-nitrobenzoateHCID 178418546HCID 178418546, 화합물HCID 178418573HCID 178418573, 화합물

생성물 1

HCID 59644399Methyl 2-acetyl-6-nitrobenzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-673a74252478423db9562632fdee041b
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07320992B2

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