Bromine → 6-Bromo-1H-indole-3-carboxylic acid

HRID 1689808Notes

Reaction equation

HRID 1689808 reaction equation
[Br:1]Br.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4]1>C(O)(=O)C>[Br:1][C:9]1[CH:10]=[C:11]2[C:6]([C:5]([C:12]([OH:14])=[O:13])=[CH:4][NH:3]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 69867Indole-3-Carboxylic Acid

Product 1

HCID 152848376-Bromo-1H-indole-3-carboxylic acidYield 60.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (49.58 g, 3100 mmol) is added slowly to a white suspension of Indole-3-carboxylic acid (50 g, 310 mmol) in 500 mL of acetic acid at room temperature, and the mixture is stirred at room temperature overnight. The solid formed is filtered and dried under vacuum for 3 hours to afford 45 g of the title compound as a grey solid (60%). MS (m/e): 240 (M+1)

Workup

  1. customThe solid formed
  2. filtrationis filtered
  3. customdried under vacuum for 3 hours

Sources & evidence

ORD record
ord-9141c0e536fe4a449feb830aa63d97e1
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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