Carbon Tetrachloride → 3-(10-Bromoanthracen-9-yl)pyridine

HRID 446655

Reaction equation

HRID 446655 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)(Cl)Cl.[Br:26]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:26][C:6]1[C:5]2[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=2)[C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[CH:11]2

Participants

6

Reactant 4

HCID 5943Carbon Tetrachloride2×HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 2643883-(Anthracen-9-yl)pyridine

Product 1

HCID 579673303-(10-Bromoanthracen-9-yl)pyridineYield 55.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a 200 mL three-necked flask were placed 1.0 g (4.0 mmol) of 3-(9-anthryl)pyridine and 25 mL of carbon tetrachloride. Under a nitrogen stream, 10 mL of a carbon tetrachloride solution containing 0.83 g (5.1 mmol) of bromine was dripped into this solution, followed by stirring at room temperature for 26 hours. After a predetermined time has passed, 100 mL of a 1.0 M sodium thiosulfate solution was added to this mixture. The aqueous layer of this mixture was extracted with chloroform. The obtained extract and the organic layer were combined and washed with a saturated aqueous solution of sodium hydrogen carbonate and with saturated brine, and dried with magnesium sulfate. This mixture was subjected to gravity filtration, and the filtrate was concentrated to give a solid. A chloroform solution of the obtained solid was suction filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina, and the filtrate was condensed to give a solid. Recrystallization of this solid from a mixed solvent of ethyl acetate and hexane gave 0.74 g of a pale yellow powder in 53% yield, which was the desired substance.

Workup

  1. customIn a 200 mL three-necked flask were placed
  2. extractionThe aqueous layer of this mixture was extracted with chloroform
  3. extractionThe obtained extract
  4. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationThis mixture was subjected to gravity filtration
  7. concentrationthe filtrate was concentrated
  8. customto give a solid
  9. filtrationfiltered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina
  10. customcondensed
  11. customto give a solid
  12. customRecrystallization of this solid from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-1b8cea19837c401982eafa7fb1054b38
Source dataset
uspto-grants-2013_07
Patent number
US08481176B2

Linked notes

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