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

HRID 633528
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HRID 633528 반응식
[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
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-026e7cc581284e2481e6449c2adaca50
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09321764B2

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