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Sodium Chloride → 2-Bromo-1-(cyclopropylmethoxy)-3-methyl-4-nitrobenzene

HRID 633528
ノート
印刷プレビュー

反応式

HRID 633528 の反応式
[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][C:3]=1[OH:12].Br[CH2:14][CH:15]1[CH2:17][CH2:16]1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][C:3]=1[O:12][CH2:14][CH:15]1[CH2:17][CH2:16]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 5234Sodium ChlorideHCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 45584722-Bromo-3-methyl-4-nitrophenol

生成物 1

HCID 867049572-Bromo-1-(cyclopropylmethoxy)-3-methyl-4-nitrobenzene収率 87.4%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

A flask with stirbar was charged with 2-bromo-3-methyl-4-nitrophenol (Parkway Scientific, 1.15 g, 4.96 mmol), (bromomethyl)cyclopropane (0.60 mL, 6.19 mmol) and cesium carbonate (2.65 g, 8.13 mmol) in dimethylformamide (16 mL). The mixture was stirred overnight at ambient temperature. The mixture was then heated to 50° C. in an oil bath. After 3 hours, the mixture was cooled and shaken in a separatory funnel with 100 mL each of ethyl acetate and saturated aqueous sodium chloride. The organics were washed twice with saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (silica gel, 0-30% ethyl acetate in hexanes) to provide 1.24 g (87%) of the title compound

後処理

  1. temperatureThe mixture was then heated to 50° C. in an oil bath
  2. waitAfter 3 hours
  3. temperaturethe mixture was cooled
  4. washThe organics were washed twice with saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (silica gel, 0-30% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-026e7cc581284e2481e6449c2adaca50
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321764B2

反応ノート

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