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

HRID 859672Notes

Reaction equation

HRID 859672 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-cc20a81dc0b447e19c3906ca43be9db0
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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