Sodium Azide → 368426-24-8

HRID 1355610Notes

Reaction equation

HRID 1355610 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 5-3, 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%). 1H NMR (CDCl3): δ 4.50 (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-eb2c39df112a45668630263f0fbf14e2
Source dataset
uspto-grants-2003_07
Patent number
US06586405B2

Reaction notes

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