4-Nitrophenol → 2-((4-Nitrophenoxy)methyl)oxirane

HRID 1989003Notes

Reaction equation

HRID 1989003 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([O-:9])=[O:8].[CH2:17]([CH:19]1[O:21][CH2:20]1)Br>>[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:19]2[CH2:20][O:21]2)=[CH:12][CH:11]=1)([O-:9])=[O:8]

Participants

4

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 18430Epibromohydrin

Product 1

HCID 213272-((4-Nitrophenoxy)methyl)oxiraneYield 51.2%

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (1.3 g, 9.6 mmol) was added to a mixture of 4-nitrophenol (1.11 g, 8 mmol) and epibromohydrin (1.37 mL, 16 mmol) The mixture was stirred at 100° C. for 18 hours. After cooling down, the residue was extracted into EtOAc. The organic layer was washed with water, brine and then dried with Na2SO4. Removal of the solvent in vacuo gave an orange residue, which was purified chromatographically on silica eluting with EtOAc/hexanes (1:10, v/v). The product was obtained as a yellow solid (0.8 g, 51%). 1H NMR (300 MHz, CDCl3) δ (ppm): 8.21 (m, 2H), 6.98 (m, 2H), 4.37 (dd, J=2.8 Hz, 11.1 Hz, 1H), 4.00 (dd, J=5.9 Hz, 11.1 Hz, 1H), 3.90 (m, 1H), 2.93 (t, J=4.8 Hz, 1H), 2.77 (dd, J=2.8 Hz, 4.8 Hz, 1H).

Workup

  1. temperatureAfter cooling down
  2. extractionthe residue was extracted into EtOAc
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried with Na2SO4
  5. customRemoval of the solvent in vacuo
  6. customgave an orange residue, which
  7. customwas purified chromatographically on silica eluting with EtOAc/hexanes (1:10

Sources & evidence

ORD record
ord-e918045e68d445fbb0a652193d49ded3
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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