Potassium Cyanide → (4-Bromo-2-ethyl-phenyl)-acetonitrile

HRID 2387062Notes

Reaction equation

HRID 2387062 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[C:4]([CH2:10][CH3:11])[CH:3]=1.[C-:12]#[N:13].[K+]>CN(C=O)C.O.CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:12]#[N:13])=[C:4]([CH2:10][CH3:11])[CH:3]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 587640754-Bromo-1-(bromomethyl)-2-ethylbenzene

Product 1

HCID 67084404(4-Bromo-2-ethyl-phenyl)-acetonitrileYield 81.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
45 °C

Procedure

To a solution of 4-bromo-1-bromomethyl-2-ethyl-benzene (2.0 g, 7.25 mmol) in DMF/H2O (30 mL/6 mL) was added potassium cyanide (471 mg, 7.25 mmol). The reaction mixture was heated to 45° C. for 3 hours before it was cooled to room temperature. The mixture was diluted with Et2O and washed with H2O, brine and dried over MgSO4. The solvent was removed in vacuo to obtain the desired product (1.33 g, 80% yield). 1H NMR (300 MHz, CDCl3): δ 1.26 (t, J=7.5 Hz, 3 H), 2.60-2.67 (m, 2 H), 3.66 (s, 2H), 7.23-7.26 (m, 1H), 7.35-7.36 (m, 1 H), 7.38-7.40 (m, 1H).

Workup

  1. temperaturewas cooled to room temperature
  2. washwashed with H2O, brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cdd54b81913245ce8c480f1fd7096fda
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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