Bromine → HCID 178467484, compound

HRID 1471853Notes

Reaction equation

HRID 1471853 reaction equation
[CH2:1]([O:3][C:4]1[NH:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=1)[CH3:2].[Br:15]Br>ClCCl>[Br:15][C:5]1[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:7][NH:8][C:4]=1[O:3][CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 178465994HCID 178465994, compound

Product 1

HCID 178467484HCID 178467484, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-ethoxy-3-phenyl-1H-pyrazole (1.0 g, 5.31 mmol) in dichloromethane (20 mL), was added bromine (0.849 g, 5.31 mmol) dropwise at room temperature. The reaction was stirred for 2 h, washed with saturated NaHCO3 solution and concentrated under reduced pressure. The residue was triturated with 10% ethyl acetate/hexane to give the title compound as a yellowish solid (1.20 g). LCMS m/z=268.07 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38 (t, J=4.2 Hz, 3H), 4.39 (q, J=4.2 Hz, 2H), 7.45-7.85 (m, 5H), 12.4 (s, 1H).

Workup

  1. washwashed with saturated NaHCO3 solution
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was triturated with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-19fcdaba31574c01bc4ce7329f7a749e
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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