Sodium Iodide → Isohexane ethyl acetate

HRID 2365582Notes

Reaction equation

HRID 2365582 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-:22].[K+].[K+].[I-].[Na+]>C(#N)C>[CH3:14][CH2:19][O:22][C:2]([CH3:10])=[O:1].[CH3:2][CH2:3][CH2:4][CH:5]([CH3:9])[CH3:6].[F:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][O:1][C:2]2[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 265484-Hydroxybenzyl cyanideHCID 5731534-Fluorophenethyl bromide

Product 2

HCID 21882781Isohexane ethyl acetateHCID 67086776HCID 67086776, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-Hydroxybenzyl cyanide (7.9 g, 59.57 mmol), 1-(2-Bromo-ethyl)-4-fluoro-benzene (17.4 g, 71.48 mmol), potassium carbonate (19.8 g, 143 mmol) and sodium iodide (2.68 g, 17.87 mmol) in acetonitrile (120 ml) is heated at reflux for 44 hours. The reaction mixture is cooled and filtered and the solvent removed in vacuo to yield a dark brown oil. Flash chromatography (SiO2, EtOAc/iso-hexane) yields {4-[2-(4-Fluoro-phenyl)-ethoxy]-phenyl}-acetonitrile as a yellow oil.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 44 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto yield a dark brown oil

Sources & evidence

ORD record
ord-ef1f0546eee64bcb8209937c9bb4bb84
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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