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

HRID 923457
ノート
印刷プレビュー

反応式

HRID 923457 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d26483e44c7f4261b2c5d8cf803a75f9
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09278968B2

反応ノート

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