Bromine → HCID 67385609, compound

HRID 1471896Notes

Reaction equation

HRID 1471896 reaction equation
[CH2:1]([C:3]1[NH:7][N:6]=[CH:5][C:4]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].[Br:14]Br>ClCCl>[Br:14][C:5]1[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:3]([CH2:1][CH3:2])[NH:7][N:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 67384438HCID 67384438, compound

Product 1

HCID 67385609HCID 67385609, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-ethyl-4-phenyl-1H-pyrazole (3.34 g, 19.39 mmol) in dichloromethane (111.0 mL), was added bromine (1.49 mL, 29.09 mmol) at 25° C. The reaction was stirred at room temperature for 72 h and quenched with NaOH (aq.) to pH 12. The organics were separated. The aqueous layer was extracted again with DCM (3×). The combined organics were washed with brine, dried (MgSO4), filtered and concentrated to give a red oil. This oil was purified by flash chromatography to give the title compound as a yellow oil (2.84 g). LCMS m/z=251.2 [M+H]+.

Workup

  1. customquenched with NaOH (aq.) to pH 12
  2. customThe organics were separated
  3. extractionThe aqueous layer was extracted again with DCM (3×)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a red oil
  9. customThis oil was purified by flash chromatography

Sources & evidence

ORD record
ord-5d0dc55d76074306b4c5080e6e94d789
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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