Bromine → HCID 59511298, compound

HRID 1157342Notes

Reaction equation

HRID 1157342 reaction equation
[C:1]1([N:7]2[CH:11]=[CH:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[Br:17]Br>C1COCC1>[Br:17][C:11]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 2700091-Phenyl-1H-1,2,3-triazoleHCID 178418339Butyllithium

Product 1

HCID 59511298HCID 59511298, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 100 ml 3 necked round bottom flask, 1-phenyl-1H-1,2,3-triazole (1.2 g) was taken in dry THF (25 ml) under nitrogen. n-Butyl lithium (3.36 ml) was added at −78° C. and stirred for 5 minutes, then bromine (3.76 ml) was added dropwise to the above reaction mixture. Reaction mixture was stirred at −78° C. for 1 hour. TLC was checked no starting material and the reaction mixture was quenched with saturated ammonium chloride (50 ml) and ethyl acetate was added. The organic layer was washed with sodium bisulphate, brine, dried and concentrated. The crude product was purified by column chromatography using pet ether & ethyl acetate as eluent to give 5-bromo-1-phenyl-1H-1,2,3-triazole as yellow solid.

Workup

  1. customReaction mixture
  2. stirringwas stirred at −78° C. for 1 hour
  3. customthe reaction mixture was quenched with saturated ammonium chloride (50 ml) and ethyl acetate
  4. additionwas added
  5. washThe organic layer was washed with sodium bisulphate, brine
  6. customdried
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-2e1339d5e6d94061a3ad3e62a314c05a
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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