Sodium Azide → HCID 178505415, compound

HRID 710080Notes

Reaction equation

HRID 710080 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N-:11]=[N+:12]=[N-:13].[Na+].CCOC(C)=O.O>CCO.[Cl-].[Zn+2].[Cl-]>[Br:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]2[NH:13][N:12]=[N:11][N:5]=2)=[C:2]([F:1])[CH:9]=1

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 7360294-Bromo-2-fluorobenzonitrileHCID 22728543Water ethylacetate

Product 1

HCID 178505415HCID 178505415, compoundYield 32.9%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 702EthanolSolvent

Procedure

2-Fluoro-4-bromobenzonitrile (300 mg, 1.5 mmol) dissolved in EtOH, added sodium azide (320 mg, 4.9 mmol), Zinc chloride (240 mg, 1.8 mmol). This mixture was stirred refluxed for 38 h. Work up (EtOAc/H2O) afforded the crude. Crude was washed with petether to obtain the titled compound (120 mg) as a white solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.89-7.79 (m, 1H), 7.59 (dd, J 1.6, 10.04, 1H), 7.45 (dd, J 1.8, 8.3, 1H).

Workup

  1. temperaturerefluxed for 38 h
  2. customafforded the crude
  3. washCrude was washed with petether

Sources & evidence

ORD record
ord-1e41b0a35ed14bab9be8ce844825e4ba
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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