1-Phenyl-1,2-propanedione → 3-Bromo-1-phenylpropane-1,2-dione

HRID 236286Notes

Reaction equation

HRID 236286 reaction equation
[C:1]1([C:7](=[O:11])[C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:12]Br>C(Cl)(Cl)Cl>[Br:12][CH2:9][C:8](=[O:10])[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:11]

Participants

4

Reactant 2

HCID 113631-Phenyl-1,2-propanedioneHCID 24408Bromine2×

Product 1

HCID 125689113-Bromo-1-phenylpropane-1,2-dioneYield 102%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
50 °C

Procedure

5.32 kg of 1-phenylpropane-1,2-dione (98.6% by G.C. equivalent to 5.24 kg, 35.4 mole) were dissolved in 36 liters of chloroform and the solution was heated to 50° C. A solution of 5.66 kg (35.4 mole) of bromine in 8 liters of chloroform was added slowly to maintain a gentle reflux and immediate decolorization of the bromine (approximately 6 hours). The solution was cooled to room temperature overnight and was washed with 20 liters of saturated sodium bicarbonate solution and 20 liters of water and dried over sodium sulfate. The solvent was removed under vacuum to obtain 8.2 kg (100% yield) of a green/yellow oil which was used directly for subsequent reactions after estimation of its purity (approximately 75% by G.C. or N.M.R.).

Workup

  1. temperatureto maintain
  2. temperaturea gentle reflux
  3. temperatureThe solution was cooled to room temperature overnight
  4. washwas washed with 20 liters of saturated sodium bicarbonate solution and 20 liters of water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-501fe104ed934cbc80f2252f8a7f9dfa
Source dataset
uspto-grants-1987_02
Patent number
US04643999

Reaction notes

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