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

HRID 2165732Notes

Reaction equation

HRID 2165732 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 were dissolved in 415 ml of methylene chloride while stirring, the solution was heated to boiling, and 144 g (0.9 mol) of bromine were added dropwise over the course of 30 minutes. The mixture was then refluxed for a further 2 hours and cooled, 400 ml of water were added, and the organic phase was 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 solution was heated
  2. temperatureThe mixture was then refluxed for a further 2 hours
  3. temperaturecooled
  4. customthe organic phase was 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-29aa9a88ca0e440185d9af77d321f89e
Source dataset
uspto-grants-1990_07
Patent number
US04940790

Reaction notes

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