Water → 2-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one

HRID 329383

Reaction equation

HRID 329383 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16](=[O:18])[CH3:17])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[Br:19]Br.O>C(Cl)Cl>[Br:19][CH2:17][C:16]([C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=1)=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 6162963',5'-Bis(tert-butyl)-4'-hydroxyacetophenone

Product 1

HCID 6161612-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

206 g (0.83 mol) of 1-(3,5-di-tert.butyl-4-hydroxyphenyl)ethanone are dissolved in 415 ml of methylene chloride while stirring, the mixture is heated to boiling, and 144 g (0.9 mol) of bromine are added dropwise over the course of 30 minutes. The mixture is then refluxed for a further 2 hours and cooled, 400 ml of water are added, and the organic phase is separated off and dried over sodium sulfate. After the solvent had been removed under reduced pressure, the solid crude product obtained was recrystallized from 540 ml of methylcyclohexane.

Workup

  1. temperaturethe mixture is heated
  2. temperatureThe mixture is then refluxed for a further 2 hours
  3. temperaturecooled
  4. customthe organic phase is separated off
  5. dry with materialdried over sodium sulfate
  6. customAfter the solvent had been removed under reduced pressure
  7. customthe solid crude product obtained
  8. customwas recrystallized from 540 ml of methylcyclohexane

Sources & evidence

ORD record
ord-72473e18e8d04ea9822d074f80995bde
Source dataset
uspto-grants-1990_01
Patent number
US04891374

Linked notes

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