Bromine → 5-(2-Bromophenyl)-1H-tetrazole

Participants

Reaction Conditions

Reaction Steps

To (tetrazol-5-yl)benzene (0.29 g) in THF (10 ml) at -25° C. was slowly added n-butyllithium (2 mL, 2.5M in hexanes) while maintaining the reaction temperature below -15° C. When the addition was over in 10 to 15 minutes, the mixture was aged at -10° C. for 30 minutes. The reaction mixture was cooled to -60° C. and bromine (0.2 mL) was added dropwise. To the reaction mixture was added aqueous 10% sodium sulfite (5 mL). An HPLC assay showed a starting material/products ratio of 3.5/96.5. The product was precipitated by the addition of water (20 mL) and acidification with 2N HCl to pH 2. The mixture was aged at 0° C. for 1 hour and filtered. The yield was 0.427 g (95%).

Provenance & Evidence