2-Bromobenzonitrile → 5-(2-Bromophenyl)-1H-tetrazole

HRID 1886061Notes

Reaction equation

HRID 1886061 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N-:10]=[N+:11]=[N-:12].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]1[NH:12][N:11]=[N:10][N:5]=1

Participants

5

Reactant 3

HCID 162722-BromobenzonitrileHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 1784193735-(2-Bromophenyl)-1H-tetrazoleYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-bromobenzonitrile (10.0 g, 0.055 mol), sodium azide (3.9 g, 0.060 mol), ammonium chloride (3.2 g, 0.060 mol), and DMF (90 mL) was heated at 100° C. for 18 h. The mixture was concentrated, taken up in water, and made basic (pH 9) with 1N KOH. The aqueous mixture was extracted with ether (discarded) and acidified with 2N HCl. The precipitate was collected by filtration to give 9.1 g (73%) of product as an off-white solid, mp 179°-181° C.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionThe aqueous mixture was extracted with ether (discarded)
  3. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-d9ff707fa43d453788a3be4c75c19965
Source dataset
uspto-grants-1992_09
Patent number
US05149699

Reaction notes

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