2-Fluoro-6-iodobenzonitrile → HCID 178505770, compound

HRID 1374155Notes

Reaction equation

HRID 1374155 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[C:4]#[N:5].[N:11]([Sn](C)(C)C)=[N+:12]=[N-:13]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[C:4]1[NH:13][N:12]=[N:11][N:5]=1

Participants

4

Reactant 2

HCID 5227222-Fluoro-6-iodobenzonitrileHCID 5104973Azido(trimethyl)stannane

Product 1

HCID 178505770HCID 178505770, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-fluoro-6-iodobenzonitrile (17.82 g, 72.15 mmol) and azidotrimethyltin (15.00 g, 72.88 mmol) in 150 mL toluene was heated to 125° C. for 72 hours. The solution was cooled to room temperature and partitioned between ethyl acetate and 0.5 N HCl. The organic extract was washed with water and brine, dried over Na2SO4, filtered and concentrated under vacuum to provide 5-(2-fluoro-6-iodophenyl)-1H-tetrazole that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 291.01 for M+H+.

Workup

  1. custompartitioned between ethyl acetate and 0.5 N HCl
  2. extractionThe organic extract
  3. washwas washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-db9ffaeed150472c8eab89063fb2d5ae
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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