Ethyl Acetate → 2-(Azidomethyl)benzonitrile

HRID 857708Notes

Reaction equation

HRID 857708 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[N-:11]=[N+:12]=[N-:13].[Na+].C(OCC)(=O)C>CN(C)C=O>[N:11]([CH2:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6])=[N+:12]=[N-:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 895992-(Bromomethyl)benzonitrile

Product 1

HCID 114919742-(Azidomethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromomethyl-benzonitrile (1.0 g, 5.1 mmol) and sodium azide (0.40 g, 6.1 mmol) in dimethylformamide (10 ml) was stirred at room temperature for 2 h. Ethyl acetate was added and the reaction mixture was washed with water and brine. Drying and solvent evaporation gave 2-azidomethyl-benzonitrile; 1H NMR (CDCl3, 400 MHz) δ 7.71 (d, 1H, J=7.7 Hz), 7.64 (m, 1H), 7.53 (d, 1H, J=7.8 Hz), 7.47 (t, 1H, J=7.6 Hz), 4.62 (s, 2H).

Workup

  1. washthe reaction mixture was washed with water and brine
  2. customDrying
  3. customsolvent evaporation

Sources & evidence

ORD record
ord-47af1a05ee8849ec9a1c97dc37b1d8fa
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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