Azido(trimethyl)stannane → 5-(2-Bromo-4-chloro-6-fluoro-phenyl)-2H-tetrazole
Reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([F:11])[C:3]=1[C:4]#[N:5].[N:12]([Sn](C)(C)C)=[N+:13]=[N-:14]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([F:11])[C:3]=1[C:4]1[N:12]=[N:13][NH:14][N:5]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 2-bromo-4-chloro-6-fluoro-benzonitrile (4 g, 17.06 mmol) and azidotrimethyltin (3.86 g, 18.77 mmol) in toluene (100 ml) was heated to 120° C. for 72 h. After completion of the reaction, the mixture was partitioned between EtOAc (50 ml) and aqueous 0.5N HCl solution (40 ml). The organic layer was separated, washed with water and brine, dried with Na2SO4 and concentrated under reduced pressure to afford the title compound (4.2 g, 87%) as red solid.
Workup
- customAfter completion of the reaction
- customthe mixture was partitioned between EtOAc (50 ml) and aqueous 0.5N HCl solution (40 ml)
- customThe organic layer was separated
- washwashed with water and brine
- dry with materialdried with Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-894b472c4021436c95b35f1bcbdda3d0
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592426B2
Reaction notes
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