Triphenylphosphine dibromide → (4-Bromo-butyl)-cyclopentane

HRID 1004646ノート

反応式

HRID 1004646 の反応式
[CH:1]1([CH2:6][CH2:7][CH2:8][CH2:9]O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:11]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[Br:11][CH2:9][CH2:8][CH2:7][CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 70579Triphenylphosphine dibromideHCID 217976434-Cyclopentylbutan-1-ol

生成物 1

HCID 22471771(4-Bromo-butyl)-cyclopentane収率 76%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 4-cyclopentyl-butan-1-ol (3.1 g, 22 mmol) in acetonitrile (200 mL) was treated with dibromotriphenylphosphorane (10.1 g, 23.9 mmol). The reaction was stirred for two hours and quenched with water (10 mL). The reaction was diluted with dichloromethane (300 mL) and washed with water (3×100 mL). The organic phase was dried (MgSO4), filtered, and concentrated to yield an oil. The product was passed through a pad of silica to yield (4-bromo-butyl)-cyclopentane as a colorless oil (3.37 g, 76%). 1H NMR (CDCl3, 300 MHz) δ 3.42 (t, 7.0 Hz, 2 H), 1.9-1.7 (m, 4 H), 1.6-1.3 (m, 9 H), 1.07 (m, 2 H).

後処理

  1. customquenched with water (10 mL)
  2. additionThe reaction was diluted with dichloromethane (300 mL)
  3. washwashed with water (3×100 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield an oil

出典と根拠

ORDレコード
ord-63974033f3584ad7ab7a7ccdab11a245
出典データセット
uspto-grants-2000_04
特許番号
US06051586

反応ノート

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