Hydrogen Bromide → HCID 14210976, compound

HRID 329384Notes

Reaction equation

HRID 329384 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH3:15])[C:8](O)=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=[O:18])C.[BrH:22]>C(Cl)(Cl)Cl.[Cu](Br)Br>[Br:22][CH2:12][C:11]([C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([OH:18])=[C:7]([CH3:15])[CH:8]=1)=[O:13]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 19872061HCID 19872061, compound

Product 1

HCID 14210976HCID 14210976, compound

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 6212ChloroformSolvent

Procedure

A solution of 82.5 g (0.4 mol) of 1-(5-tert.butyl-3-methyl-hydroxyphenyl)-ethanone in 360 ml of chloroform was added dropwise while stirring to a suspension, heated to boiling, of 179 g (0.8 mol) of copper(II) bromide in 360 ml f ethyl acetate. The mixture was subsequently refluxed for 4 hours until the evolution of hydrogen bromide was complete. After the mixture had been cooled to room temperature, the copper salts were filtered off under suction, the filter residue was washed repeatedly with ethyl acetate, the filtrate was evaporated under reduced pressure, the solid residue was recrystallized from cyclohexane.

Workup

  1. temperatureheated
  2. filtrationthe copper salts were filtered off under suction
  3. washthe filter residue was washed repeatedly with ethyl acetate
  4. customthe filtrate was evaporated under reduced pressure
  5. customthe solid residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-546ac2fde452403188be09561e766184
Source dataset
uspto-grants-1990_01
Patent number
US04891374

Reaction notes

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