Sulfuric Acid → 5-[(4-Bromophenyl)methyl]-2-(1,1-dimethylethyl)-2H-tetrazole

HRID 1647057Notes

Reaction equation

HRID 1647057 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[N:10]=[N:11][NH:12][N:13]=2)=[CH:4][CH:3]=1.[C:14](O)([CH3:17])([CH3:16])[CH3:15].FC(F)(F)C(O)=O.S(=O)(=O)(O)O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[N:10]=[N:11][N:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[N:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 6422Trifluoroacetic acidHCID 148887005-((4-bromophenyl)methyl)-1H-1,2,3,4-tetrazole

Product 1

HCID 148887015-[(4-Bromophenyl)methyl]-2-(1,1-dimethylethyl)-2H-tetrazoleYield 54%

Procedure

A mixture of 5-[(4-bromophenyl)methyl]-2H-tetrazole (18.5 g, 77 mmol), t-butanol (11.4 g, 150 mmol), trifluoroacetic acid (76 mL, 1.0 mol) and concentrated sulfuric acid (3.8 g, 39 mmol) was stirred for 24 h and then partitioned between ethyl acetate (250 mL) and water (100 mL). The organic layer was washed with water (4×100 mL) and 1M NaOH (2×100 mL) and was dried over sodium sulfate. Filtration and removal of the solvent in vacuo produced a solid that was recrystallized from hexane to give 5-[(4-bromophenyl)methyl]-2-(1,1-dimethylethyl)-2H-tetrazole. (12.3 g, 47 mmol) in 54% yield, mp. 69°-70° C.

Workup

  1. custompartitioned between ethyl acetate (250 mL) and water (100 mL)
  2. washThe organic layer was washed with water (4×100 mL) and 1M NaOH (2×100 mL)
  3. dry with materialwas dried over sodium sulfate
  4. filtrationFiltration and removal of the solvent in vacuo
  5. customproduced a solid
  6. customthat was recrystallized from hexane

Sources & evidence

ORD record
ord-98633bf30d9048ffab5653a7cbff4b93
Source dataset
uspto-grants-1993_01
Patent number
US05182263

Reaction notes

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