Benzonitrile, 4-bromo- → 5-(4-Bromophenyl)-1H-tetrazole

HRID 1721248Notes

Reaction equation

HRID 1721248 reaction equation
[Br:1][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+].[NH4+].[Cl-]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]2[N:10]=[N:11][NH:12][N:7]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 12162Benzonitrile, 4-bromo-HCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 7661415-(4-Bromophenyl)-1H-tetrazoleYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromobenzonitrile (20 g, 110 mmol), sodium azide (7.9 g, 121 mmol) and NH4Cl (6.5 g, 121 mmol) in DMF (340 mL) were heated at 90° C. under argon. After 2 days the reaction mixture was concentrated and then diluted with water (300 mL). After adding enough 1M NaOH to render the mixture basic (litmus paper) it was washed with ether (4×25 mL). The aqueous portion was acidified to pH 3 with 1N HCl, the precipitated product was collected by suction filtration and then washed with water. The crude product was recrystallized from ethanol to give crystalline 5-(4-bromophenyl)-2H-tetrazole (19.2 g, 83.6 mmol) in 76% yield, mp. 271°-273° C.

Workup

  1. concentrationAfter 2 days the reaction mixture was concentrated
  2. additiondiluted with water (300 mL)
  3. additionAfter adding enough 1M NaOH to render the mixture basic (litmus paper) it
  4. washwas washed with ether (4×25 mL)
  5. filtrationthe precipitated product was collected by suction filtration
  6. washwashed with water
  7. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-3e5c6e1c29174c17bdcef0e01c4bd55c
Source dataset
uspto-grants-1996_04
Patent number
US05508437

Reaction notes

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