Fenipentol → (1-Bromopentyl)benzene

HRID 628264Notes

Reaction equation

HRID 628264 reaction equation
P(Br)(Br)[Br:2].[C:5]1([CH:11](O)[CH2:12][CH2:13][CH2:14][CH3:15])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CCOCC>[Br:2][CH:11]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 3338FenipentolHCID 24614Phosphorus tribromide

Product 1

HCID 10900349(1-Bromopentyl)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

PBr3 (0.171 mL, 1.82 mmol, Aldrich) was added to a solution of 1-phenylpentan-1-ol (0.500 g, 3.04 mmol, Alfa Aesar) in Et2O (3.2 mL) at 0° C. The reaction was allowed to reach ambient temperature and then was quenched with ice water and diluted with hexanes. The layers were separated and the organic layer was washed with water and then with brine, dried over sodium sulfate, filtered and concentrated. Flash chromatography, eluting with hexanes afforded product (0.15 g, 22%).

Workup

  1. customto reach ambient temperature
  2. customwas quenched with ice water
  3. additiondiluted with hexanes
  4. customThe layers were separated
  5. washthe organic layer was washed with water
  6. dry with materialwith brine, dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washFlash chromatography, eluting with hexanes afforded product (0.15 g, 22%)

Sources & evidence

ORD record
ord-48cca4ff248444dc9b37fc291373a27a
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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