Bromine → 3-Bromo-7-(2,4-dichloro-phenyl)-2-methyl-2h-indazole

HRID 902549Notes

Reaction equation

HRID 902549 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:17]2[C:13](=[CH:14][N:15]([CH3:18])[N:16]=2)[CH:12]=[CH:11][CH:10]=1.[Br:19]Br>C(O)(=O)C>[Br:19][C:14]1[N:15]([CH3:18])[N:16]=[C:17]2[C:13]=1[CH:12]=[CH:11][CH:10]=[C:9]2[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 115297297-(2,4-dichloro-phenyl)-2-methyl-2H-indazole

Product 1

HCID 112912283-Bromo-7-(2,4-dichloro-phenyl)-2-methyl-2h-indazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 7-(2,4-dichloro-phenyl)-2-methyl-2H-indazole (0.659 g, 2.38 mmol) in 2 mL of acetic acid was added bromine (0.122 mL, 2.38 mmol) dropwise. The yellow-orange solution was stirred for 15 m, in which time an orange solid precipitated. The mixture was concentrated to a yellow solid, which was partitioned between 20 mL of a 10% aqueous NaOH solution and 20 mL of diethyl ether. The organic layer was washed with 20 mL of a saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated to a yellow-stained white solid. Column chromatography (0→10% EtOAc/hexanes) afforded 3-bromo-7-(2,4-dichloro-phenyl)-2-methyl-2H-indazole as a white solid (24: Ar=2,4-dichlorophenyl; 0.525 g; 62%; m.p. 137-139).

Workup

  1. customprecipitated
  2. concentrationThe mixture was concentrated to a yellow solid, which
  3. customwas partitioned between 20 mL of a 10% aqueous NaOH solution and 20 mL of diethyl ether
  4. washThe organic layer was washed with 20 mL of a saturated aqueous NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to a yellow-stained white solid

Sources & evidence

ORD record
ord-559290d400db46559b14194bed35477a
Source dataset
uspto-grants-2008_04
Patent number
US07365211B2

Reaction notes

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