Bromine → HCID 67384797, compound

HRID 1471879Notes

Reaction equation

HRID 1471879 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[NH:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=1.[Br:16]Br>C(Cl)Cl>[Br:16][C:6]1[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][NH:9][C:5]=1[CH2:4][CH2:3][O:2][CH3:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 67384805HCID 67384805, compound

Product 1

HCID 67384797HCID 67384797, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(2-methoxyethyl)-3-phenyl-1H-pyrazole (2.0 g, 9.89 mmol) in DCM (100 mL) was added bromine (4.74 g, 29.7 mmol) dropwise at 0° C. The reaction was stirred at 0° C. for 1 h and then at room temperature for 2 h before quenching with Na2SO3 (10% aqueous). The organic phase was removed and the aqueous layer was extracted with DCM (2×50 mL). The organic layers were combined, washed with brine, dried over MgSO4, and concentrated to give the title compound (2.5 g). LCMS m/z=281.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.87 (t, J=6.82 Hz, 2H), 3.27 (s, 3H), 3.62 (t, J=6.82 Hz, 2H), 5.75 (s, 1H), 7.35-7.51 (m, 3H), 7.75-7.82 (m, 2H).

Workup

  1. customat room temperature for 2 h before quenching with Na2SO3 (10% aqueous)
  2. customThe organic phase was removed
  3. extractionthe aqueous layer was extracted with DCM (2×50 mL)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ae5e0debf28248fe800fc2457694a305
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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