Nitric Acid → 4-Bromo-2-tert-butyl-6-nitrophenol

HRID 1295958

Reaction equation

HRID 1295958 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=1.CCOCC>CCCCCC>[Br:5][C:6]1[CH:11]=[C:10]([N+:1]([O-:4])=[O:2])[C:9]([OH:12])=[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 3283Diethyl EtherHCID 970684-Bromo-2-tert-butylphenol

Product 1

HCID 229297864-Bromo-2-tert-butyl-6-nitrophenol

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Concentrated nitric acid (112 ml) was gradually added dropwise to a solution of 4-bromo-2-(tert-butyl)phenol (485 g) in hexane (3000 ml) while cooling on ice. After stirring for 2 hours at below 20° C., ether (2000 ml) was added and the reaction mixture was washed with water. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. Hexane was added to the residue and the precipitated crystals were filtered to yield the title compound (418 g) as yellow crystals.

Workup

  1. temperaturewhile cooling on ice
  2. washthe reaction mixture was washed with water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionHexane was added to the residue
  6. filtrationthe precipitated crystals were filtered

Sources & evidence

ORD record
ord-efe05d74fd684ec882f43fd4e5e5b462
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Linked notes

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