Water → Ethyl 3-Bromoindole-2-carboxylate

HRID 1013280Notes

Reaction equation

HRID 1013280 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[Br:15]N1C(=O)CCC1=O.O>C1COCC1>[Br:15][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 4715017Ethyl 3-Bromoindole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl-2-indole carboxylate (1.89 g) and N-bromosuccinimide (1.77 g) in THF (30 mL) was stirred at room temperature for 1 hour. The mixture was poured into water (150 mL) and filtered. The filtrant was washed with THF, dried under vacuum at 60° C., and recrystallized from ethyl acetate/hexanes.

Workup

  1. filtrationfiltered
  2. washThe filtrant was washed with THF
  3. customdried under vacuum at 60° C.
  4. customrecrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c738334f151648c7b816ff2e468ec645
Source dataset
uspto-grants-2011_07
Patent number
US07981888B2

Reaction notes

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