3-Nitrophenol → 4-(3-Nitro-phenoxymethyl)-biphenyl

HRID 499752Notes

Reaction equation

HRID 499752 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-

Product 1

HCID 165692534-(3-Nitro-phenoxymethyl)-biphenyl

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-Nitro-phenol (3.5 g, 25 mmole), 4-Bromomethyl-biphenyl (4.94 g, 20 mmole) and Potassium carbonate (3.8 g, 30 mmole) in 75 mL of acetone is stirred for 16 hr at room temperature. After removal of the solvent, the residue is taken up in ethyl acetate, washed with 1 N NaOH and brine, dried over Na2SO4, and concentrated to yield a solid. The solid is washed with methanol and dried under vacuum to afford 4-(3-Nitro-phenoxymethyl)-biphenyl.

Workup

  1. customAfter removal of the solvent
  2. washwashed with 1 N NaOH and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto yield a solid
  6. washThe solid is washed with methanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-e29b0e4f72bf484fbb746b36c5a256f0
Source dataset
uspto-grants-2010_08
Patent number
US07767706B2

Reaction notes

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