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

HRID 633528Notes

Reaction equation

HRID 633528 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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

Workup

  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)

Sources & evidence

ORD record
ord-026e7cc581284e2481e6449c2adaca50
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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