Water → HCID 58251653, 화합물

HRID 37754노트

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HRID 37754 반응식
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][CH:3]=1.[C:14]1([C:24]2[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>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.O1CCCC1>[CH3:13][O:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:27]2[CH:28]=[CH:29][C:24]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=[CH:16][CH:15]=3)=[CH:25][CH:26]=2)=[CH:3][CH:4]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1385211-Bromo-4-methoxynaphthaleneHCID 441193994-(1-Naphthyl)phenylboronic Acid (contains varying amounts of Anhydride)

생성물 1

HCID 58251653HCID 58251653, 화합물수율 52.6%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매2회HCID 8028Tetrahydrofuran용매

실험 절차

1-Bromo-4-methoxynaphthalene (25 g, 0.105 mol), 4-(naphthalen-1-yl)phenylboronic acid (30.4 g, 0.137 mol), potassium carbonate (21.9 g, 0.16 mol), tetrakis(triphenylphosphine)palladium(0) (2.4 g, 0.01 mol), water (25 mL), tetrahydrofuran (75 mL) and toluene (75 mL) were stirred in a 250 mL round-bottom flask for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (300 mL) and water (1000 mL). The organic layer was dried with magnesium sulfate and concentrated under reduced pressure to obtain a solid. The solid was dissolved in hot toluene (400 mL) and then filtered. The filtrate was recrystallized in methanol (800 mL). The resultant solid was filtered and washed with hexane (300 mL) to obtain a product (20 g, 0.055 mol, 52.6%).

후처리

  1. temperatureunder reflux
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate (300 mL) and water (1000 mL)
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain a solid
  7. filtrationfiltered
  8. customThe filtrate was recrystallized in methanol (800 mL)
  9. filtrationThe resultant solid was filtered
  10. washwashed with hexane (300 mL)

출처 및 근거

ORD 기록
ord-ea826ef5f5ee438782a80e86607ef50a
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524381B2

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