Bromine → HCID 67384464, compound

HRID 1471897Notes

Reaction equation

HRID 1471897 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([CH2:12][CH2:13][CH3:14])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15]Br>ClCCl>[Br:15][C:11]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][NH:9][C:10]=1[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 24408BromineHCID 67384982HCID 67384982, compound

Product 1

HCID 67384464HCID 67384464, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-phenyl-5-propyl-1H-pyrazole (3.83 g, 20.56 mmol) in dichloromethane (118.0 mL) was added bromine (1.05 mL, 20.56 mmol) at 25° C. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was then quenched with 2 M Na2CO3 (aq.) to pH 12 and the organics were separated. The aqueous layer was extracted with DCM (thrice). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a red oil. This oil was purified by silica gel flash chromatography to give the title compound as a yellow oil (3.44 g). LCMS m/z=265.1, 267.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 0.97 (t, J=7.33 Hz, 3H), 1.63-1.74 (m, 2H), 2.57 (t, J=7.58 Hz, 2H), 7.37-7.48 (m, 3H), 7.77-7.82 (m, 2H).

Workup

  1. customThe reaction mixture was then quenched with 2 M Na2CO3 (aq.) to pH 12
  2. customthe organics were separated
  3. extractionThe aqueous layer was extracted with DCM (thrice)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a red oil
  9. customThis oil was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-58ed4f1c3edf435ebd217442a9cefa28
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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