1-Bromonaphthalene → 1-Cyclopropylnaphthalene

HRID 448138

반응식

HRID 448138 반응식
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1>O1CCCC1.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]1([C:15]2[C:16]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 70011-BromonaphthaleneHCID 178418630HCID 178418630, 화합물

생성물 1

HCID 146686931-Cyclopropylnaphthalene수율 76%

시약·촉매·용매 2

HCID 178418745HCID 178418745, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Cyclopropylmagnesium bromide (150 mL, 0.5 M in tetrahydrofuran) was slowly added to a solution of 1-bromo-naphthalene (10 g, 50 mmol) and [1,3-bis(diphenylphosphino)propane]dichloronickel(II) in tetrahydrofuran (10 mL) stirred at 0° C. The reaction mixture was stirred at room temperature for 16 hours and the solvent was evaporated under reduced pressure. EtOAc and ammonium chloride in water were added. After extraction, the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield 1-cyclopropyl-naphthalene (6.4 g, 76%).

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 16 hours
  2. customthe solvent was evaporated under reduced pressure
  3. additionEtOAc and ammonium chloride in water were added
  4. extractionAfter extraction
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-ccdd59be48a541a9a605a6921766dcd4
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481581B2

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