Bromine → HCID 178524081, compound

HRID 1198973Notes

Reaction equation

HRID 1198973 reaction equation
[C:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([OH:3])=[O:2].[Br:13]Br.S(=O)(O)[O-].[Na+]>C(O)(=O)C.[Cl-].[Na+].O>[Br:13][C:8]1[C:7]2[C:11](=[CH:12][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=2)[NH:10][N:9]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 162279381H-indazole-6-carboxylic acidHCID 23665763Sodium Bisulfite

Product 1

HCID 178524081HCID 178524081, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 6-carboxyindazole (4.0 g) in acetic acid (140 ml) was added bromine (1.53 ml), and the mixture was stirred in the dark for 24 hours. After the addition of saturated sodium bisulfite (50 ml) and brine (100 ml), the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated. The resulting solid was powdered and vacuum dried to afford 3-bromo-6-carboxyindazole as a light brown solid (5.88 g, 99%), mp >250°.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customvacuum dried

Sources & evidence

ORD record
ord-a7626a0437e54ac4b5e5a681c5276f41
Source dataset
uspto-grants-1990_02
Patent number
US04898863

Reaction notes

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