Bromine → HCID 178468563, compound

HRID 592305Notes

Reaction equation

HRID 592305 reaction equation
[NH:1]1[C:5]2[CH:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[Br:15]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.C(O)(=O)C>[Br:15][C:9]1[C:4]2[N:3]=[N:2][NH:1][C:5]=2[CH:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=1

Participants

6

Reactant 3

HCID 24408Bromine2×HCID 24477Sodium ThiosulfateHCID 178468695HCID 178468695, compound

Product 1

HCID 178468563HCID 178468563, compoundYield 10.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 1H-1,2,3-benzotriazole-6-carboxylate (5.0 g, 26.2 mmol) in dichloromethane (25.2 mL) was purged with nitrogen and a solution of bromine (1.35 mL, 26.2 mmol) in acetic acid (5.17 mL) was added dropwise. The mixture was stirred at ambient temperature. After 18 h, additional bromine (0.67 mL, 13.1 mmol) was added and the mixture was stirred at ambient temperature. After 18 h, saturated aqueous sodium thiosulfate was added and the mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.025% trifluoroacetic acid) gave the title compound (0.73 g): LC-MS [M]=270.0.

Workup

  1. stirringthe mixture was stirred at ambient temperature
  2. waitAfter 18 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.025% trifluoroacetic acid)

Sources & evidence

ORD record
ord-ebb9835cb145430a852bfab887e73702
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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