Ammonia → 3-Bromo-5-ethylbenzonitrile

HRID 539299Notes

Reaction equation

HRID 539299 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=[C:4]([Br:10])[CH:3]=1.[Cu](C#N)[C:12]#[N:13].N1C=CC=CC=1.N>CN(C=O)C.O>[Br:10][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH2:8][CH3:9])[CH:5]=1)[C:12]#[N:13]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 1049PyridineHCID 187118073,5-DibromoethylbenzeneHCID 178418260HCID 178418260, compound

Product 1

HCID 679795883-Bromo-5-ethylbenzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1,3-dibromo-5-ethylbenzene (2.7 g, 10.2 mmol), copper cyanide (0.916 g, 10.2 mmol), pyridine (1.65 mL, 20.5 mmol) in DMF (15 mL) was heated at 150° C. for 3 h. After cooling to r.t., the mixture was poured into a solution of H2O (30 mL) and ammonia (25% aq. Solution, 20 mL) and extracted with EtOAc. The combined organic layer was dried (MgSO4), filtered and concentrated in vacuo. The product was purified using flash chromatography on silica gel, gradient elution of 0-60% EtOAc in n-heptane. GCMS (CI) m/z 210 [M+1]+.

Workup

  1. temperatureAfter cooling to r.t.
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was purified
  7. washon silica gel, gradient elution of 0-60% EtOAc in n-heptane

Sources & evidence

ORD record
ord-b95a28911d2b45b0addc82afb37b60d6
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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