4-Nitrophenol → 1-[(8-Bromooctyl)oxy]-4-nitrobenzene

HRID 1482724Notes

Reaction equation

HRID 1482724 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].[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br>CC(C)=O>[Br:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][O:16][C:13]1[CH:14]=[CH:15][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 783101,8-Dibromooctane

Product 1

HCID 132191191-[(8-Bromooctyl)oxy]-4-nitrobenzeneYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Anhydrous K2CO3 (5.50 g, 39.8 mmol) was added to a stirred solution of 4-nitrophenol (3.69 g, 26.5 mmol) and 1,8-dibromooctane (36.00 g, 132.1 mmol) in acetone. The reaction mixture was heated at reflux 12 h, then cooled to ambient temperature and filtered. The residue was washed with acetone (3×15 mL) and the combined organic layers evaporated in vacuo. The residue was dissolved in EtOAc (50 mL), the solution washed with water (2×20 mL), brine, dried over Na2SO4, filtered, volatiles evaporated in vacuo, and the residue subjected to column chromatography on silica gel (230-400 mesh) using hexanes as elutant to afford 7.75 g (23.5 mmol, 89%) of product as a low melting solid, mp 39-40° C. 1H NMR (500 MHz, CDCl3) δ 1.35-1.50 (m, 8H), 1.79-1.89 (m, 4H), 3.41 (t, J=6.5 Hz, 2H), 4.04 (t, J=6.5 Hz, 2H), 6.93 (d, J=10 Hz, 2H), 8.18 (d, J=9.5, 2H); 13C NMR (125 MHz, CDCl3) δ 27.9, 28.5, 28.8, 29.0, 29.2, 32.6, 33.9, 68.7, 114.3, 125.8, 129.3, 141.2, 164.1; HRMS (EI) calculated for C14H20BrNO3 [M]+0 329.6027, observed 329.6040.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux 12 h
  3. filtrationfiltered
  4. washThe residue was washed with acetone (3×15 mL)
  5. customthe combined organic layers evaporated in vacuo
  6. dissolutionThe residue was dissolved in EtOAc (50 mL)
  7. washthe solution washed with water (2×20 mL), brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customvolatiles evaporated in vacuo

Sources & evidence

ORD record
ord-f0893c3439ad495d8a49072ea69ce57f
Source dataset
uspto-grants-2016_08
Patent number
US09415110B1

Reaction notes

Loading…