Carbon Tetrachloride → HCID 12274172, compound

HRID 355423Notes

Reaction equation

HRID 355423 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][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:24])[C:12]=2[CH:11]=1.C(Cl)(Cl)(Cl)Cl>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>[Br:1][CH2:9][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:24])[C:12]=2[CH:11]=1

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 2234732-Methylxanthen-9-one

Product 1

HCID 12274172HCID 12274172, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 962WaterSolvent

Procedure

Benzoyl peroxide (4.6 g, 19 mmol) and N-bromosuccinimide (67.6 g, 380 mmol) were added to a mixture of 2-methyl-9H-xanthen-9-one (79.9 g, 380 mmol) and carbon tetrachloride (800 ml) with heating under reflux, and the mixture was stirred for 4 hours. After spontaneous cooling to room temperature, water was added to the reaction mixture, and the reaction product was extracted with chloroform. The extract was washed with saturated sodium bicarbonate aqueous solution, water and saturated sodium chloride aqueous solution in that order, dried over anhydrous magnesium sulfate, and then concentrated under a reduced pressure. The resulting residue was recrystallized from ethyl acetate to give the title compound (78.3 g, 271 mmol, 71%) as yellow crystals.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. extractionthe reaction product was extracted with chloroform
  4. washThe extract was washed with saturated sodium bicarbonate aqueous solution, water and saturated sodium chloride aqueous solution in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3c3626e484a442759f6aeddab0aca5e9
Source dataset
uspto-grants-1998_11
Patent number
US05830902

Reaction notes

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