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

HRID 607218

Reaction equation

HRID 607218 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-6fe3cbac73b641a0bd7308394b078e25
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Linked notes

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