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

HRID 23413

Reaction equation

HRID 23413 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[Br:13]Br>C(O)(=O)C>[Br:13][C:7]1[CH:8]=[C:9]2[C:4]([C:3]([C:10]([OH:12])=[O:11])=[CH:2][NH:1]2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 69867Indole-3-Carboxylic Acid

Product 1

HCID 152848376-Bromo-1H-indole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

To a solution of indole-3-carboxylic acid (4.81 g, 30 mmole) in acetic acid (50 ml), bromine was added dropwise with stirring at 15° C. After stirring overnight at room temperature the reaction mixture was set aside without stirring for 24 hours during which time pure product crystallized from solution. The precipitate was collected and dried to afford 1.29 g pure 6-bromoindole-3-carboxylic acid. The mother liquor was poured into water (250 ml) and another crop of product was obtained (3.84 g) as a 1:1 mixture of the 6-bromo- and the 5-bromoindole-3-carboxylic acid.

Workup

  1. stirringAfter stirring overnight at room temperature the reaction mixture
  2. stirringwithout stirring for 24 hours during which time pure product
  3. customcrystallized from solution
  4. customThe precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-041984c22f354fbca34f7500f39174d9
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Linked notes

Loading…