Boron tribromide → Methyl 4-hydroxy-1H-indole-2-carboxylate

HRID 1929025Notes

Reaction equation

HRID 1929025 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([O:14]C)[CH:10]=[CH:9][CH:8]=2)=[O:4].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([OH:14])[CH:10]=[CH:9][CH:8]=2)=[O:4]

Participants

5

Reactant 3

HCID 25134Boron tribromide2×HCID 516892Sodium BicarbonateHCID 688172methyl 4-methoxy-1H-indole-2-carboxylate

Product 1

HCID 22310940Methyl 4-hydroxy-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of 4-Methyloxy-1H-indole-2-carboxylic acid methyl ester (1 g, 4.87 mmol) in DCM (10 ml) is added BBr3 (1M in DCM, 4.9 ml, 4.9 mmol). It is stirred for 1 hour and another equivalent (4.9 ml) of BBr3 is added. After another hour, the mixture is poured on ice and the pH is adjusted to 7 with sodium bicarbonate. Extraction with DCM gave a yellow powder.

Workup

  1. waitAfter another hour
  2. additionthe mixture is poured on ice
  3. extractionExtraction with DCM
  4. customgave a yellow powder

Sources & evidence

ORD record
ord-ffb2a2edfa854a3589f664e4134ec901
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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