1-Bromonaphthalene → 1-Cyclopropylnaphthalene

HRID 551342

反応式

HRID 551342 の反応式
[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

参加物

5

反応物 2

HCID 70011-BromonaphthaleneHCID 178418630HCID 178418630、化合物

生成物 1

HCID 146686931-Cyclopropylnaphthalene収率 76%

試薬・触媒・溶媒 2

HCID 178418745HCID 178418745、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-13db7488c62f433e84dcd70a8261dcfa
出典データセット
uspto-grants-2011_05
特許番号
US07947721B2

関連ノート

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