N-bromobutanimide → Ethyl 3-Bromoindole-2-carboxylate

HRID 1013292Notes

Reaction equation

HRID 1013292 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[Br:15]N1C(=O)CCC1=O>O1CCCC1>[Br:15][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][C:2]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

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

Product 1

HCID 4715017Ethyl 3-Bromoindole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 1H-indole-2-carboxylate (9.45 g) in tetrahydrofuran (100 mL) was added N-bromosuccinimide (8.89 g, 50 mmol). The mixture was stirred at room temperature for 1 hour. The mixture was concentrated under vacuum and the residue was dissolved with water (100 ml) and diethyl ether (300 ml). The organic layer was washed with water brine and dried over Na2SO4. After filtration, concentration of solvent afforded the title compound.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved with water (100 ml) and diethyl ether (300 ml)
  3. washThe organic layer was washed with water brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration, concentration of solvent

Sources & evidence

ORD record
ord-55764f20deef48b9b0933d6d565b73fb
Source dataset
uspto-grants-2011_07
Patent number
US07981888B2

Reaction notes

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