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

HRID 901892Notes

Reaction equation

HRID 901892 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-098f4ce333374394911a6fb87a1d78f7
Source dataset
uspto-grants-2008_04
Patent number
US07365068B2

Reaction notes

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