Bromine → 3-(10-Bromoanthracen-9-yl)pyridine

HRID 535239

반응식

HRID 535239 반응식
[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.[Br:21]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:21][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

참가 물질

5

반응물 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 2643883-(Anthracen-9-yl)pyridine

생성물 1

HCID 579673303-(10-Bromoanthracen-9-yl)pyridine

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매2회

실험 절차

In a 200 μL three-neck flask, 1.0 g (4.0 mmol) of 3-(9-anthryl)pyridine and 25 mL of carbon tetrachloride were placed. Then, 10 μL of a carbon tetrachloride solution containing 0.83 g (5.1 mmol) of bromine was dripped into the solution under nitrogen stream, and the solution was stirred for 26 hours at room temperature. After a certain period, 100 mL of a 1.0 M sodium thiosulfate solution was added into the mixture. Then, an aqueous layer of the mixture was extracted with chloroform. The obtained extracted solution and the organic layer were combined, washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and dried with magnesium sulfate. The mixture was gravity filtered, and the obtained filtrate was condensed to give a solid. A chloroform solution of the solid was subjected to suction filtration 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. The solid was recrystallized with ethyl acetate/hexane, so that 0.74 g of target pale yellow powder was obtained in a yield of 53%.

후처리

  1. waitAfter a certain period
  2. extractionThen, an aqueous layer of the mixture was extracted with chloroform
  3. extractionThe obtained extracted solution
  4. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. customcondensed
  8. customto give a solid
  9. filtrationA chloroform solution of the solid was subjected to suction filtration 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. customThe solid was recrystallized with ethyl acetate/hexane, so that 0.74 g of target pale yellow powder
  13. customwas obtained in a yield of 53%

출처 및 근거

ORD 기록
ord-28897b69340440fe8320452abdb690e3
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859108B2

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