Potassium Carbonate → 1-Nitro-3-(3-bromo-phenoxymethyl)-benzene

HRID 883970Notes

Reaction equation

HRID 883970 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[Br:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([CH2:7][O:19][C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([Br:12])[CH:14]=2)[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 12078alpha-Chloro-m-nitrotoluene

Product 1

HCID 283695411-Nitro-3-(3-bromo-phenoxymethyl)-benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-nitrobenzyl chloride (1.0 g, 5.83 mmol), 3-bromophenol (1.01 g, 5.83 mmol) and potassium carbonate (806 mg, 5.83 mmol) in acetone (25 mL) was heated to reflux for 23 hours. After cooling the solid was filtered off and the filtrate was concentrated under vacuum to a yellow residue which was dissolved in ethyl acetate (50 mL) and washed with 1N aqueous sodium hydroxide solution (25 mL) and water (25 mL) then dried and concentrated under vacuum to the title compound as a white solid (1.64 g, 91%).

Workup

  1. temperatureto reflux for 23 hours
  2. temperatureAfter cooling the solid
  3. filtrationwas filtered off
  4. concentrationthe filtrate was concentrated under vacuum to a yellow residue which
  5. dissolutionwas dissolved in ethyl acetate (50 mL)
  6. washwashed with 1N aqueous sodium hydroxide solution (25 mL) and water (25 mL)
  7. customthen dried
  8. concentrationconcentrated under vacuum to the title compound as a white solid (1.64 g, 91%)

Sources & evidence

ORD record
ord-66b0cb8a4f3b4e9786205d036dcc245f
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

Loading…