Sulfuric Acid → 1-tert-Butyl-5-(2-bromophenyl)-1H-tetrazole

HRID 1886062Notes

Reaction equation

HRID 1886062 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][N:11]=[N:10][N:9]=1.[CH3:13][C:14](O)([CH3:16])[CH3:15].OS(O)(=O)=O>FC(F)(F)C(O)=O>[C:14]([N:9]1[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])=[N:12][N:11]=[N:10]1)([CH3:16])([CH3:15])[CH3:13]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 1784193735-(2-Bromophenyl)-1H-tetrazole

Product 1

HCID 218408841-tert-Butyl-5-(2-bromophenyl)-1H-tetrazoleYield 67.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 5-(2-bromophenyl)-1H-tetrazole (7.9 g, 0.035 mol) in trifluoroacetic acid (35 mL) was added tBuOH (5.2 g, 0.070 mol) and H2SO4 (1.0 mL, 0.0175 mol). After 18 h, the solution was concentrated and the residue was taken up in EtOAc. The mixture was washed with water, 2.5N NaOH, water, dried (MgSO4), and concentrated. Purification by flash chromatography (20% EtOAc/hexane) gave 6.6 g (67%) of product as a pale yellow oil.

Workup

  1. concentrationthe solution was concentrated
  2. washThe mixture was washed with water, 2.5N NaOH, water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification by flash chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-f68114dee73a4de982dab59f03da1590
Source dataset
uspto-grants-1992_09
Patent number
US05149699

Reaction notes

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