4-Nitrophenol → 2-[(4-Nitrophenoxy)methyl]pyridine

HRID 1725715Notes

Reaction equation

HRID 1725715 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24]Br>CC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 27347202-(Bromomethyl)pyridine hydrobromide

Product 1

HCID 8209312-[(4-Nitrophenoxy)methyl]pyridineYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A dry reaction flask was charged with 4-nitrophenol (3.858 g, 27.75 mmol), anhydrous K2CO3 (8.29 g, 60 mmol) and acetone (250 mL). To this heterogeneous mixture was added 2-pyridylmethylbromide hydrobromide (7.0 g, 27.75 mmol) and refluxed for 24 h. From the resulting reaction mixture, 200 mL of acetone was removed under reduced pressure. The resulting residue was then diluted with ice-water (1 liter), the solid crushed out was filtered, washed with water and dried well to give 2-[(4-nitrophenoxy)methyl]pyridine (6.05 g, 95% yield). 1H NMR (CDCl3): δ 8.61 (d, 1H, J=4.8 Hz), 8.19 (d, 2H, J=9.0 Hz), 7.72 (m, 2H), 7.46 (d, 1H, J=7.8 Hz), 7.25 (m, 1H), 7.05 (d, 2H, J=9.3 Hz), 5.28 (s, 2H); LCMS (m/z): 231 (MH+).

Workup

  1. customA dry reaction flask
  2. temperaturerefluxed for 24 h
  3. customwas removed under reduced pressure
  4. additionThe resulting residue was then diluted with ice-water (1 liter)
  5. customthe solid crushed out
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried well

Sources & evidence

ORD record
ord-dd320376d62c448698936cf9320ca905
Source dataset
uspto-grants-2009_02
Patent number
US07491732B2

Reaction notes

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