反应详情

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.

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)