Hydrogen Bromide → 7,9a-Dibromo-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone

HRID 2051412Notes

Reaction equation

HRID 2051412 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]2[C:14]=1[C:13](=[O:15])[CH:12]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11]1.[BrH:17].[Br:18]Br>C(O)(=O)C>[Br:17][C:3]1[C:2]([OH:1])=[C:14]2[C:6]([CH:7]3[C:12]([Br:18])([C:13]2=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8]3)=[C:5]([CH3:16])[CH:4]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 15157186HCID 15157186, compound

Product 1

HCID 151571897,9a-Dibromo-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.50 Grams of 8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone was dissolved in 50 ml of acetic acid and to the solution were gradually added dropwise 0.2 ml of hydrobromic acid and 1.3 ml of bromine, followed by refluxing under heating for 1 hour. The reaction mixture was poured into ice water and extracted with chloroform. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution in this order and then dried with magnesium sulfate. The solvent was distilled off and the residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:10) and then recyrstallized from ethanol to obtain 3.86 g of 7,9a-dibromo-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone.

Workup

  1. temperatureby refluxing
  2. temperatureunder heating for 1 hour
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution in this order
  5. dry with materialdried with magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:10)

Sources & evidence

ORD record
ord-e73e9678e7b548ad9961ad03c300b3dc
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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