1-Bromopentane → HCID 21472391, compound

HRID 2294971Notes

Reaction equation

HRID 2294971 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:10]([O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 80571-Bromopentane2×HCID 108944-IodophenolHCID 11430Potassium Carbonate

Product 1

HCID 21472391HCID 21472391, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-iodophenol (6.6 g), 1-bromopentane (4.5 g), anhydrous potassium carbonate (13.8 g) and acetone (100 ml) was stirred at reflux for 24 hours, with the additions of a further quantity of 1-bromopentane after 4 hours (4.5 g) and 8 hours (4.5 g). The acetone was removed by evaporation. The residue was triturated with water (50 ml) and extracted with ether (3×30 ml). The organic extracts were combined, dried (MgSO4) and evaporated. The residue, a colourless oil, was distilled at 160° C. and 0.05 mm pressure (using a Kugelrohr oven) to give 4-n-pentyloxyiodobenzene as a colourless oil (7.8 g); microanalysis, found C, 45.7; H, 5.4%; C11H15IO requires: C, 45.5; H, 5.2%; NMR(DMSO-d6): 0.84-0.95(3H,t), 1.25-1.48(4H,m), 1.62-1.77(2H,m), 3.88-3.97(2H,t), 6.72-6.8(2H,d), 7.52-7.6(2H,d); m/z 290 (M).

Workup

  1. customThe acetone was removed by evaporation
  2. customThe residue was triturated with water (50 ml)
  3. extractionextracted with ether (3×30 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. distillationThe residue, a colourless oil, was distilled at 160° C.

Sources & evidence

ORD record
ord-8502d848bd0b4d02b3972501d7f8754d
Source dataset
uspto-grants-1997_11
Patent number
US05691349

Reaction notes

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