Bromine → HCID 178511395, compound

HRID 1471905Notes

Reaction equation

HRID 1471905 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([O:12][CH2:13][C:14]#[N:15])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:16]Br>ClCCl>[Br:16][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[O:12][CH2:13][C:14]#[N:15]

Participants

4

Reactant 2

HCID 24408BromineHCID 178511383HCID 178511383, compound

Product 1

HCID 178511395HCID 178511395, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-phenyl-1H-pyrazol-5-yloxy)acetonitrile (0.500 g, 2.51 mmol) in dichloromethane (15.0 mL), was added bromine (0.129 mL, 2.51 mmol) at 25° C. The reaction was stirred at room temperature for 1 h and quenched with 2 M Na2CO3 (aq.) to pH 12. The organics were separated. The aqueous layer was extracted 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 silica gel flash chromatography to give the title compound as a yellow solid (0.360 g). LCMS m/z=278.1, 280.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 5.21 (s, 2H), 7.39-7.61 (m, 3H), 7.70-7.77 (m, 2H), 13.04 (s, 1H).

Workup

  1. customquenched with 2 M Na2CO3 (aq.) to pH 12
  2. customThe organics were separated
  3. extractionThe aqueous layer was extracted 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 silica gel flash chromatography

Sources & evidence

ORD record
ord-e649edcc6a7e447eb3a964271f924732
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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