Water → Ethyl 7-chloro-5-hydroxyindole-2-carboxylate

HRID 1791681Notes

Reaction equation

HRID 1791681 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:16]C)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.B(Br)(Br)Br.O.[OH-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([OH:16])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 22030809Ethyl 7-chloro-5-methoxyindole-2-carboxylate

Product 1

HCID 22030936Ethyl 7-chloro-5-hydroxyindole-2-carboxylateYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of ethyl 7-chloro-5-methoxyindole-2-carboxylate (82 mg, 0.323 mmol) in dichloromethane (5 ml) at −78° C. was added boron tribromide (1.07 ml of a 1.0M solution in DCM, 1.07 mmol) and the reaction stirred at −78° C. for 30 minutes then allowed to warm to ambient temperature overnight. Water was carefully added and the pH adjusted to pH 6–7 by addition of 2M sodium hydroxide. The mixture was extracted with ethyl acetate (2×50 ml), and the organic solution washed with brine, dried (MgSO4), filtered and evaporated to give ethyl 7-chloro-5-hydroxyindole-2-carboxylate (55 mg, 71%) as an orange solid.

Workup

  1. temperatureto warm to ambient temperature overnight
  2. extractionThe mixture was extracted with ethyl acetate (2×50 ml)
  3. washthe organic solution washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-b84b0cbdfc1d47a3b0b638876f5a0ba5
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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