Potassium Cyanide → 2,5-Dichlorobenzyl cyanide

HRID 2043716Notes

Reaction equation

HRID 2043716 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4]Br.[C-:11]#[N:12].[K+]>C(O)C.O>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4][C:11]#[N:12]

Participants

5

Conditions

Temperature
80 °C

Procedure

A mixture of 2,5-dichlorobenzyl bromide (5.4 g, 22.5 mmol) in 16 mL of ethanol and potassium cyanide (1.63 g, 25 mmol) in 4 mL of water was heated at 80° C. overnight, then cooled, and the solids were filtered and washed with ethanol to give 3.5 g of 2,5-dichlorophenylacetonitrile as a white powder melting at 89-91° C. The nitrile was suspended in 20 red, of ethanol, and 20 mL of a 25% aqueous NaOH solution was added. The mixture was heated in a CEM Explore™ microwave reactor at 140° C. for 30 minutes, then cooled, poured into ice water and acidified to pH 1 with concentrated HCl to give a precipitate. The precipitate was filtered, washed with water and dried in a vacuum oven at 90° C. for 5 h to give the title compound as a white powder.

Workup

  1. temperaturecooled
  2. filtrationthe solids were filtered
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-1650e19846b54c33875d992443f0bb64
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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