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

HRID 1004646노트

반응식

HRID 1004646 반응식
[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

참가 물질

4

반응물 2

HCID 70579Triphenylphosphine dibromideHCID 217976434-Cyclopentylbutan-1-ol

생성물 1

HCID 22471771(4-Bromo-butyl)-cyclopentane수율 76%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-63974033f3584ad7ab7a7ccdab11a245
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06051586

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