Sodium Azide → 368426-24-8

HRID 1263429Notes

Reaction equation

HRID 1263429 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[CH2:14]Br)[C:9]#[N:10]>CN(C=O)C>[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[CH2:14][N:1]=[N+:2]=[N-:3])[C:9]#[N:10]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 27831494-(Bromomethyl)-3-fluorobenzonitrile2×

Product 1

HCID 18506744368426-24-8Yield 86.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (Aldrich, 0.63 g, 9.8 mmol) was added to a solution of 3-fluoro-4-(bromomethyl)benzonitrile (compound 39, 1.4 g, 6.5 mmol) in DMF (15 mL). After stirring at ambient temperature for 20 hours, the reaction mixture was partitioned in EtOAc and water (100 mL, each). Organic layer was then dried (MgSO4), and solvent was removed under vacuum to give the title compound (0.995 g, 86%). 1HNMR (CDCl3) δ4.50 (s, 2H), 7.38 (d, 2H, J=8.1 Hz), 7.52 (m, 2H).

Workup

  1. customthe reaction mixture was partitioned in EtOAc
  2. dry with materialOrganic layer was then dried (MgSO4), and solvent
  3. customwas removed under vacuum

Sources & evidence

ORD record
ord-a5dd4943d6fe4865a5bbd7b3df0695b2
Source dataset
uspto-grants-2003_04
Patent number
US06541467B1

Reaction notes

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