4-Fluorobenzonitrile → 4-azidobenzonitrile

HRID 2202104Notes

Reaction equation

HRID 2202104 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[N-:10]=[N+:11]=[N-:12].[Na+]>CS(C)=O.O>[N:10]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)=[N+:11]=[N-:12]

Participants

5

Reactant 2

HCID 145174-FluorobenzonitrileHCID 33557Sodium Azide

Product 1

HCID 5756914-azidobenzonitrileYield 49%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 4-fluorobenzonitrile (10.0 g, 82.57 mmol, 1.00 equiv) and NaN3 (6.0 g, 92.29 mmol, 1.12 equiv) in DMSO (100 mL) was stirred at 100° C. for 2 h. The reaction was cooled to room temperature and then diluted with 700 mL of water. The precipitate was collected by filtration and air-dried to give 5.8 g (49%) of 4-azidobenzonitrile as a light yellow solid. 1H NMR (300 MHz, DMSO-d6) δ: 7.88 (d, J=13.5 Hz, 2H), 7.31 (d, J=13.5 Hz, 2H) ppm.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customair-dried

Sources & evidence

ORD record
ord-00813be924184cfb99aebcf79d2126e4
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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