Bromine → 9-Bromo-10-(4-trifluoromethylphenyl)anthracene

HRID 1928974Notes

Reaction equation

HRID 1928974 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[C:15]([CH:16]=[C:17]4[C:22]=2[CH:21]=[CH:20][CH:19]=[CH:18]4)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:5][CH:4]=1.[Br:25]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:25][C:16]1[C:17]2[C:22]([C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:23])([F:24])[F:1])=[CH:8][CH:7]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:21][CH:20]=[CH:19][CH:18]=2

Participants

5

Procedure

5.7 g (18 mmol) of 9-(4-trifluoromethylphenyl)anthracene and 90 mL of carbon tetrachloride were put into a 500-mL three-neck flask and stirred. A solution in which 3.2 g (20 mmol) of bromine was dissolved in 10 mL of carbon tetrachloride was dropped into the above solution through a dropping funnel. After that, the solution was stirred at the room temperature for 1 hour, and a sodium thiosulfate aqueous solution was added to the reaction solution to complete the reaction. A water layer of the reaction mixture was extracted by chloroform, and the extracted solution and an organic layer were together washed with a saturated sodium hydrogen carbonate solution and saturated saline. The organic layer was dried with magnesium sulfate, and the mixture was filtrated naturally to remove the magnesium sulfate. Then, the filtrate was condensed to obtain a solid. The obtained solid was recrystallized with ethanol, whereby 5.9 g of a yellow powdery solid, which was a target matter, was obtained with the yield of 84%.

Workup

  1. additionwas dropped into the above solution through a dropping funnel
  2. stirringAfter that, the solution was stirred at the room temperature for 1 hour
  3. customthe reaction
  4. extractionA water layer of the reaction mixture was extracted by chloroform
  5. washthe extracted solution and an organic layer were together washed with a saturated sodium hydrogen carbonate solution and saturated saline
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. filtrationthe mixture was filtrated naturally
  8. customto remove the magnesium sulfate
  9. customcondensed
  10. customto obtain a solid
  11. customThe obtained solid was recrystallized with ethanol, whereby 5.9 g of a yellow powdery solid, which
  12. customwas obtained with the yield of 84%

Sources & evidence

ORD record
ord-1a30691f77504676bb91748707fda123
Source dataset
uspto-grants-2012_05
Patent number
US08183793B2

Reaction notes

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