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

HRID 454156Notes

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

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

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

Sources & evidence

ORD record: ord-9c40a5aa93694b5b9d5151fdae252965
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492560B2

Reaction notes

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