2-Nitrophenol → 1-(Benzhydryloxy)-2-nitrobenzene

HRID 132589

Reaction equation

HRID 132589 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].Br[CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[K].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH:12]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 5462222Potassium

Product 1

HCID 74341221-(Benzhydryloxy)-2-nitrobenzeneYield 39.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of o-nitrophenol (2.08 g, 15.0 mmol), 1-[bromo(phenyl)methyl]benzene (3.70 g, 15.0 mmol) and potassium carbonated (K2CO3) (4.14 g, 30.0 mmol) in acetone (60 mL) was kept at reflux temperature for 5 h. The reaction mixture was cooled to room temperature, concentrated in vacuo. The residue was partitioned between dichloromethane (CH2Cl2) and water (H2O), organic layer dried over sodium sulphate (Na2SO4), filtered, concentrated. The residue was purified by silica gel flash chromatography to give subtitled compound (1.81 g).

Workup

  1. temperatureat reflux temperature for 5 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between dichloromethane (CH2Cl2) and water (H2O), organic layer
  4. dry with materialdried over sodium sulphate (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-079031298525448db5b6e52e03b4a7e2
Source dataset
uspto-grants-2008_06
Patent number
US07388020B2

Linked notes

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