Potassium Cyanide → 4-Iodophenylacetonitrile

HRID 1488313Notes

Reaction equation

HRID 1488313 reaction equation
[C-:1]#[N:2].[K+].[I:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[CH:7][CH:6]=1>>[I:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][C:1]#[N:2])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 9032Potassium CyanideHCID 9542584-Iodobenzyl bromide

Product 1

HCID 1428664-Iodophenylacetonitrile

Procedure

A mixture of potassium cyanide (33.23 g, Sigma-Aldrich) and 4-iodobenzyl bromide (101 g, Apollo Scientific) in 3:1 IMS/water (1 L) was heated to reflux for 2 hours then cooled to room temperature. The organics were removed in vacuo and the aqueous was extracted with EtOAc (2×750 mL). The combined organics were washed with brine (300 mL), dried (magnesium sulphate) and concentrated in vacuo to give the product as oil that solidified on standing. Yield: 78.4 g. 1H NMR (400 MHz, CDCl3): δ 7.71 (2H, d, ArH), 7.08 (2H, d, ArH) 3.66 (2H, s, ArCH2CN).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. customThe organics were removed in vacuo
  4. extractionthe aqueous was extracted with EtOAc (2×750 mL)
  5. washThe combined organics were washed with brine (300 mL)
  6. dry with materialdried (magnesium sulphate)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d0e07fabb2240f08ed22dcd440765fe
Source dataset
uspto-grants-2016_08
Patent number
US09431145B2

Reaction notes

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