Toluene → 2-{4-[10-(1-Naphthyl)-9-anthryl]phenyl}benzoxazole

HRID 535242노트

반응식

HRID 535242 반응식
Br[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[O:23][C:24]4[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=4[N:26]=3)=[CH:18][CH:17]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[C:31]1(B(O)O)[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[C:31]1([C:2]2[C:3]3[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:9]([C:16]3[CH:17]=[CH:18][C:19]([C:22]4[O:23][C:24]5[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=5[N:26]=4)=[CH:20][CH:21]=3)=[C:10]3[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]3)[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 57967305HCID 57967305, 화합물

생성물 1

HCID 579673692-{4-[10-(1-Naphthyl)-9-anthryl]phenyl}benzoxazole수율 78.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매2회

실험 절차

In a 50 mL three-neck flask, 0.90 g (2.0 mmol) of 2-[4-(10-bromo-9-anthryl)phenyl]benzoxazole, 0.37 g (2.2 mmol) of 1-naphthaleneboronic acid, 0.50 g (4.7 mmol) of sodium carbonate, 10 mL of toluene, 3 mL of ethanol, and 3 mL of water were placed. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. To the mixture, 32 mg (0.027 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was stirred under nitrogen stream at 80° C. for 7 hours. After a certain period, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extracted solution and the organic layer were combined and washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and the organic layer was dried with magnesium sulfate. The mixture was gravity filtered, and the obtained filtrate was condensed to give a solid. The solid was purified by silica gel column chromatograghy (toluene:hexane=2:1) and recrystallized with toluene/hexane, giving 0.78 g of the target pale yellow powder in a yield of 78%.

후처리

  1. customThe mixture was degassed
  2. stirringthe mixture was stirred under nitrogen stream at 80° C. for 7 hours
  3. waitAfter a certain period
  4. extractionan aqueous layer was extracted with toluene
  5. extractionThe obtained extracted solution
  6. washwashed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline
  7. dry with materialthe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. customcondensed
  10. customto give a solid
  11. customThe solid was purified by silica gel column chromatograghy (toluene:hexane=2:1)
  12. customrecrystallized with toluene/hexane

출처 및 근거

ORD 기록
ord-2766f3b3e8bf4841ac36c467a6cc47c6
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859108B2

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