Bromine → 5-(2-Bromophenyl)-1H-tetrazole
Reaction equation
[NH:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N:4][N:3]=[N:2]1.C([Li])CCC.[Br:17]Br.S([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[Br:17][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:5]1[NH:1][N:2]=[N:3][N:4]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -60 °C
Procedure
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%).
Workup
- customat -25° C.
- temperaturewhile maintaining the reaction temperature below -15° C
- additionWhen the addition
- customwas over in 10 to 15 minutes
- customThe product was precipitated by the addition of water (20 mL) and acidification with 2N HCl to pH 2
- waitThe mixture was aged at 0° C. for 1 hour
- filtrationfiltered
Sources & evidence
- ORD record
- ord-055542b469c041908211449d023662b1
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05039814
Reaction notes
Loading…