Diethyl Ether → Oxirane, ((5-methyl-2-nitrophenoxy)methyl)-

HRID 496212

Reaction equation

HRID 496212 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].C[CH2:19][O:20][CH2:21][CH3:22]>CN(C=O)C.C(C1OC1)Br>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:7]=1)[O:8][CH2:22][CH:21]1[CH2:19][O:20]1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 127886-Nitro-m-cresol

Product 1

HCID 153034Oxirane, ((5-methyl-2-nitrophenoxy)methyl)-Yield 83%

Reagents, catalysts & solvents 2

HCID 18430EpibromohydrinCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-Methyl-2-nitrophenol (7.7 g, 50 mmol), potassium carbonate (13.8 g, 0.1 mmol) and epibromohydrine (8.25 mL, 0.1 mmol) was dissolved in DMF (100 mL) and stirred 2-3 h at 100° C. under an atmosphere of nitrogen. The mixture was diluted with ether (0.5L) and extracted with water until pH=7. The organic phase was evaporated and the residue was purified by flash-chromatography on silica (DCM) to give the sub-title compound as a yellow solid (8.65 g, 83%).

Workup

  1. extractionextracted with water until pH=7
  2. customThe organic phase was evaporated
  3. customthe residue was purified by flash-chromatography on silica (DCM)

Sources & evidence

ORD record
ord-fb52fea343044fd4b0211f5acc6755f7
Source dataset
uspto-grants-2005_09
Patent number
US06943188B2

Linked notes

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