Potassium Iodide → HCID 22227850, compound

HRID 1744492Notes

Reaction equation

HRID 1744492 reaction equation
[I-].[K+].[CH2:3]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)[C:4]([CH3:7])([CH3:6])[CH3:5].[Br:18]Br>O>[Br:18][C:14]1[CH:13]=[C:12]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:10][C:9]=1[O:8][CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 24408BromineHCID 14255179HCID 14255179, compound

Product 1

HCID 22227850HCID 22227850, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Subsequently, a catalytic amount of potassium iodide was added to 4-neopentyloxynitrobenzene (69 g), and bromine (66 g) was added dropwise at 60° C. The mixture was stirred for 5 h. The reaction mixture was poured into water and extracted with toluene. The organic layer was washed with aqueous sodium sulfite solution, dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was recrystallized from n-hexane to give 3-bromo-4-neopentyloxynitrobenzene (80 g), melting point: 86–88° C.

Workup

  1. additionwas added dropwise at 60° C
  2. extractionextracted with toluene
  3. washThe organic layer was washed with aqueous sodium sulfite solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter which the solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-41b7008b25fa4a8e9af3320aead145c1
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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