Sulfuric Acid → 5-(4-bromophenyl)-2-(1,1-dimethylethyl)-2H-tetrazole

HRID 487819Notes

Reaction equation

HRID 487819 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][NH:11][N:12]=2)=[CH:4][CH:3]=1.[C:13](O)([CH3:16])([CH3:15])[CH3:14].S(=O)(=O)(O)O>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][N:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 7661415-(4-Bromophenyl)-1H-tetrazole

Product 1

HCID 148887285-(4-bromophenyl)-2-(1,1-dimethylethyl)-2H-tetrazoleYield 71%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5-(4-Bromophenyl)-2H-tetrazole (19.0 g. 81.9 mmol), t-butanol (12.1 g. 164 mmol). trifluoroacetic acid (80 mL) and concentrated sulfuric acid (4.6 g, 41 mmol) were stirred at ambient temperature for 24 hours. The mixture was concentrated and dissolved in ethyl acetate (200 mL). After washing with water (3×25 mL), 1M NAOH (3×25 mL) and brine (25 mL) the organic layer was dried (Na2SO4), filtered and concentrated. The oil was purified by chromatography on a Waters Prep 500 liquid chromatograph fitted with two silica gel cartridges eluting with a mixture of hexanes and ethyl acetate (9:1) to provide 5-(4-bromophenyl)-2-(1,1-dimethylethyl)-2H-tetrazole (17.1 g. 58.1 mmol) as a yellow oil in 71% yield.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in ethyl acetate (200 mL)
  3. washAfter washing with water (3×25 mL), 1M NAOH (3×25 mL) and brine (25 mL) the organic layer
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe oil was purified by chromatography on a Waters Prep 500 liquid chromatograph
  8. customfitted with two silica gel cartridges
  9. washeluting with a mixture of hexanes and ethyl acetate (9:1)

Sources & evidence

ORD record
ord-21aaa84053044a5f9744cd744f6cc1dc
Source dataset
uspto-grants-1994_03
Patent number
US05296608

Reaction notes

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