2-Methoxyethanol → HCID 10377392, compound

HRID 1085162Notes

Reaction equation

HRID 1085162 reaction equation
Br[CH2:2][C:3]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]([CH3:12])[N:4]=1.[CH3:13][O:14][CH2:15][CH2:16][OH:17]>F[B-](F)(F)F.[Ag+]>[CH3:13][O:14][CH2:15][CH2:16][O:17][CH2:2][C:3]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]([CH3:12])[N:4]=1

Participants

4

Reactant 2

HCID 80192-MethoxyethanolHCID 102643161H-Pyrazole, 3-(bromomethyl)-5-chloro-1-methyl-4-nitro-

Product 1

HCID 10377392HCID 10377392, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 159722Silver tetrafluoroborateCatalyst

Procedure

3-Bromomethyl-5-chloro-1-methyl-4-nitropyrazole (2.42 g, 9.5 mmoles), and silver tetrafluoroborate (2.22 g, 11.4 mmoles), were stirred at reflux in 2-methoxyethanol (25 ml) for 6 hours. The black solid was filtered off and the solvent removed under reduced pressure. The oil was dissolved in ethyl acetate (100 ml) and washed with water (100 ml). The organic phase was dried over magnesium sulphate and the solvent removed under reduced pressure. The product was purified by chromatography on silica eluting with 10% ethyl acetate in dichloromethane. Fractions containing product were evaporated yielding the title compound as a white solid (1.54 g, 65%).

Workup

  1. filtrationThe black solid was filtered off
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe oil was dissolved in ethyl acetate (100 ml)
  4. washwashed with water (100 ml)
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. customthe solvent removed under reduced pressure
  7. customThe product was purified by chromatography on silica eluting with 10% ethyl acetate in dichloromethane
  8. additionFractions containing product
  9. customwere evaporated

Sources & evidence

ORD record
ord-4b14dd97f3154bd78a14bb25e283a39b
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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