Hydrochloric Acid → HCID 178419483, compound

HRID 1835830Notes

Reaction equation

HRID 1835830 reaction equation
[Br:1]Br.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4]1.S(=O)(O)[O-].[Na+].Cl>[OH-].[Na+]>[Br:1][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:3][N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 92211H-IndazoleHCID 24408BromineHCID 23665763Sodium Bisulfite

Product 1

HCID 178419483HCID 178419483, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

A solution of bromine (0.99 g, 6.19 mmol) in 10% NaOH was slowly added to a suspension of indazole (1 g, 8.50 mmol) in 2 N NaOH (25 mL). The reaction mixture became a thick white slurry. After stirring for 2 hours, a small amount of sodium bisulfite was added and the solution was neutralized with 1 N HCl. The white solid was filtered and washed with water. Recrystallization from water gave 0.76 g (45% yield) of 3-bromoindazole 4a:

Workup

  1. filtrationThe white solid was filtered
  2. washwashed with water
  3. customRecrystallization from water

Sources & evidence

ORD record
ord-5fd308489b4441c49289ebde94e5a67c
Source dataset
uspto-grants-2004_08
Patent number
US06774134B2

Reaction notes

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