Bromine → 2-Bromo-9-xanthenone

HRID 1779133Notes

Reaction equation

HRID 1779133 reaction equation
S([O-])([O-])=O.[Na+].[Na+].BrBr.[Br:9][C:10]1[CH:23]=[CH:22][C:21]2[O:20][C:19]3[C:14](=[CH:15][C:16](Br)=[CH:17][CH:18]=3)[C:13](=[O:25])[C:12]=2[CH:11]=1>C(Cl)(Cl)Cl>[Br:9][C:10]1[CH:23]=[CH:22][C:21]2[O:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[O:25])[C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 363840HCID 363840, compound

Product 1

HCID 50689632-Bromo-9-xanthenoneYield 41%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

The reaction solution was refluxed for 5 hours at 100° C. under heating and stirring in a nitrogen atmosphere. Upon completion of the reaction, chloroform and a saturated aqueous sodium sulfite solution were added to the reaction solution and stirring was continued until the color of bromine was lost. The organic layer was separated, washed with a saturated aqueous sodium carbonate solution, dried with magnesium sulfate, and filtered. The solvent in the filtrate was distilled away at a reduced pressure. The precipitated solid was purified with a silica gel column (toluene: 100%). As a result, 2.9 g (yield: 41%) of 2-bromoxanthone and 2.2 (yield: 25%) g of 2,7-dibromoxanthone were obtained.

Workup

  1. temperatureunder heating
  2. stirringstirring
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous sodium carbonate solution
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. distillationThe solvent in the filtrate was distilled away at a reduced pressure
  8. customThe precipitated solid was purified with a silica gel column (toluene: 100%)

Sources & evidence

ORD record
ord-68c2f266db164b3796528f12cb1801e7
Source dataset
uspto-grants-2016_02
Patent number
US09269911B2

Reaction notes

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