Hydrogen Bromide → HCID 14210976, compound

HRID 2165734Notes

Reaction equation

HRID 2165734 reaction equation
[C:1]([C:5]1[C:6]([OH:15])=[C:7]([CH3:14])[CH:8]=[C:9]([C:11](=[O:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[BrH:16]>C(Cl)(Cl)Cl.C(OCC)(=O)C.[Cu](Br)Br>[Br:16][CH2:12][C:11]([C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([OH:15])=[C:7]([CH3:14])[CH:8]=1)=[O:13]

Participants

6

Reactant 2

HCID 260Hydrogen BromideHCID 23043212HCID 23043212, compound

Product 1

HCID 14210976HCID 14210976, compound

Reagents, catalysts & solvents 3

HCID 24611Copper bromide (CuBr2)CatalystHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 82.5 g (0.4 mol) of 1-(5-tert.butyl-3-methyl-4-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 of 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, and 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-b758009e14db4fdf8645bde33eec2691
Source dataset
uspto-grants-1990_07
Patent number
US04940790

Reaction notes

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