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

HRID 1071174Notes

Reaction equation

HRID 1071174 reaction equation
[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

Participants

4

Reactant 2

HCID 70579Triphenylphosphine dibromideHCID 217976434-Cyclopentylbutan-1-ol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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, 2H), 1.9-1.7 (m, 4H), 1.6-1.3 (m, 9H), 1.07 (m, 2H).

Workup

  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

Sources & evidence

ORD record
ord-b5f51980639f45d28710b6260d01c6be
Source dataset
uspto-grants-2005_06
Patent number
US06903218B2

Reaction notes

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