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Nitroethane → Benzoic acid, 4-(1-nitroethyl)-, methyl ester

HRID 923457
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HRID 923457 반응식
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[N+:12]([CH2:15][CH3:16])([O-:14])=[O:13].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].COCCOC>[N+:12]([CH:15]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1)[CH3:16])([O-:14])=[O:13]
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참가 물질

8

반응물 5

HCID 6587NitroethaneHCID 10796Cesium carbonateHCID 12081Methyl 4-bromobenzoateHCID 25517Ammonium ChlorideHCID 27349372-(Di-tert-butylphosphino)-2'-methyl-1,1'-biphenyl

생성물 1

HCID 11310314Benzoic acid, 4-(1-nitroethyl)-, methyl ester

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 80711,2-Dimethoxyethane용매

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온도
60 °C

실험 절차

A mixture of 2.0 g of methyl 4-bromobenzoate, 1.3 ml of nitroethane, 172 mg of tris(dibenzylideneacetone)dipalladium(0), 232 mg of 2-(di-tert-butylphosphino)-2′-methylbiphenyl, 3.33 g of cesium carbonate, and 44 ml of 1,2-dimethoxyethane (DME) was stirred at 60° C. for 18 hours. The reaction mixture was left to be cooled to room temperature, followed by adding a saturated aqueous ammonium chloride solution and extracting with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.44 g of methyl 4-(1-nitroethyl)benzoate.

후처리

  1. waitThe reaction mixture was left
  2. temperatureto be cooled to room temperature
  3. extractionextracting with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was then evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-d26483e44c7f4261b2c5d8cf803a75f9
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09278968B2

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