Potassium tert-butoxide → 2-Bromo-4-chloro-1-(2-methylenecyclopentyloxy)benzene

HRID 1909527ノート

反応式

HRID 1909527 の反応式
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:9]=1[O:10][CH:11]1[CH2:15][CH2:14][CH2:13][C:12]1=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[Br:7][C:8]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:9]=1[O:10][CH:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[CH2:1]

参加物

5

反応物 2

HCID 23665647Potassium tert-butoxideHCID 585667782-(2-Bromo-4-chlorophenoxy)cyclopentanone

生成物 1

HCID 585666372-Bromo-4-chloro-1-(2-methylenecyclopentyloxy)benzene収率 58.2%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To the mixture of methyl triphenylphosphonium bromide (16.0 g, 44.8 mmol) in anhydrous tetrahydrofuran (125 mL) at 0° C. under nitrogen was added portion wise the potassium tert-butoxide (5.0 g, 44.8 mmol). After stirring at 0° C. for 30 minutes, the mixture of 2-(2-bromo-4-chlorophenoxy)cyclopentanone (516B) (10.8 g, 37.3 mmol) in tetrahydrofuran (40 mL) was added slowly. The resulting mixture was stirred at room temperature under nitrogen for 3 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic phase was washed with water, brine, dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5-10% EtOAc in hexanes) to provide 2-bromo-4-chloro-1-(2-methylenecyclopentyloxy)benzene (517) (6.2 g, 58.2%) as a colorless oil.

後処理

  1. additionwas added slowly
  2. stirringThe resulting mixture was stirred at room temperature under nitrogen for 3 hours
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with water, brine
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (5-10% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-531e431aeae441e8865d511c3b961724
出典データセット
uspto-grants-2013_12
特許番号
US08598374B2

反応ノート

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