Chloroform → HCID 178526560, compound

HRID 706535Notes

Reaction equation

HRID 706535 reaction equation
C([O-])(=O)C.[Na+].[N+:6]([C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][NH:13]2)([O-:8])=[O:7].C(Cl)(Cl)Cl.[Br:22]Br>C(O)(=O)C>[Br:22][C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[CH:17][C:9]=2[N+:6]([O-:8])=[O:7])[NH:13][N:12]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 180574-NitroindazoleHCID 24408BromineHCID 517045Sodium Acetate

Product 1

HCID 178526560HCID 178526560, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a flask equipped with a mechanical stirrer was added sodium acetate (26.4 g, 0.306 mol), 4-nitro-1H-indazole (50 g, 0.306 mol), 300 mL of acetic acid and 300 mL of chloroform. Bromine (51.4 g, 0.322 mol) in 60 mL of acetic acid was added to the reaction mixture over 3.5 hours, while the temperature was kept under 25° C. The reaction mixture was stirred for two hours, then concentrated under reduced pressure. Water (500 mL) was added to the resulting solids. The solids were collected by filtration, washed with 500 mL of water, and dried under vacuum to give 68 g (92%) of 3-bromo-4-nitro-1H-indazole.

Workup

  1. customTo a flask equipped with a mechanical stirrer
  2. customwas kept under 25° C
  3. concentrationconcentrated under reduced pressure
  4. additionWater (500 mL) was added to the resulting solids
  5. filtrationThe solids were collected by filtration
  6. washwashed with 500 mL of water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-e0d269bd8f6d4f6bac49c663220fd58c
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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