Hydrochloric Acid → 2,10-Di(2-naphthyl)anthracene

HRID 68514

반응식

HRID 68514 반응식
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.C([Li])CCC.[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[C:27]1[CH:40]=[CH:39][C:38]2[C:37](=O)[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30][C:29]=2[CH:28]=1.Cl>C1COCC1.CCCCCC>[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[C:27]1[CH:40]=[CH:39][C:38]2[C:29](=[CH:30][C:31]3[C:36]([C:37]=2[C:2]2[CH:11]=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:3]=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:28]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 113722-BromonaphthaleneHCID 581944502-(2-Naphthyl)-10-anthroneHCID 178418339Butyllithium

생성물 1

HCID 581942762,10-Di(2-naphthyl)anthracene수율 32%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

Under an argon atmosphere, a solution of 4.81 g of 2-bromonaphthalene in 30 mL of THF was cooled to −78° C. Subsequently, 25 mL of a 1.6-M solution of n-butyllithium in hexane were dropped to the solution, and then the mixture was stirred at −78° C. for 1 hour. A solution of 6.76 g of 2-(2-naphthyl)-10-anthrone in 20 mL of THF was added to the mixture, and then the resultant reaction solution was stirred for 5 hours at 50° C. under heat. After the reaction solution had been cooled to room temperature, 100 mL of 10% hydrochloric acid were added to the solution. After the water layer had been removed, the organic layer was washed with water and a saturated salt solution. Then, the organic layer was dried with magnesium sulfate. The solvent was removed by distillation under reduced pressure, and then the residue was purified by silica gel column chromatography. Thus, 2.90 g of 2,10-di(2-naphthyl)anthracene were obtained (in 32% yield).

후처리

  1. customthe resultant reaction solution
  2. stirringwas stirred for 5 hours at 50° C.
  3. temperatureunder heat
  4. temperatureAfter the reaction solution had been cooled to room temperature
  5. customAfter the water layer had been removed
  6. washthe organic layer was washed with water
  7. dry with materialThen, the organic layer was dried with magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ad9f616da4e343db967793d8c8e55f3d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822041B2

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