Potassium Iodide → 2-Bromo-1-(2-methylpropoxy)-4-nitrobenzene

HRID 1744514Notes

Reaction equation

HRID 1744514 reaction equation
[I-].[K+].[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[CH:4]([CH3:6])[CH3:5].[Br:17]Br>O>[CH2:3]([O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[Br:17])[CH:4]([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 24408BromineHCID 13049719HCID 13049719, compound

Product 1

HCID 137497902-Bromo-1-(2-methylpropoxy)-4-nitrobenzeneYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Subsequently, a catalytic amount of potassium iodide was added to 4-isobutoxynitrobenzene (203 g) and the mixture was heated to 60° C. Bromine (183 g) was added dropwise over 3 h. The mixture was stirred further for 1 h. The reaction mixture was poured into water and extracted with toluene. The organic layer was washed with aqueous sodium sulfite solution and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The obtained oily substance was distilled under reduced pressure to give 2-isobutoxy-5-nitrobromobenzene (248 g), boiling point: 135–140° C./0.25 mmHg.

Workup

  1. extractionextracted with toluene
  2. washThe organic layer was washed with aqueous sodium sulfite solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. distillationThe obtained oily substance was distilled under reduced pressure

Sources & evidence

ORD record
ord-b38bfa3662334ae3b68aca53b2915fed
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

Loading…