Water → 2-bromo-1H-indole

HRID 493245Notes

Reaction equation

HRID 493245 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2C(OCC)=O)(=O)=O)C=CC=CC=1.[Br:24]Br.O>CN(C=O)C>[Br:24][C:11]1[NH:10][C:18]2[C:13]([CH:12]=1)=[CH:14][CH:15]=[CH:16][CH:17]=2

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 506886Ethyl 1-(benzenesulfonyl)indole-2-carboxylate

Product 1

HCID 118056312-bromo-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of ethyl 1-phenylsulfonylindole-2-carboxylate (1 eq.) in DMF (2.5 ml/mmol) under N2, was added a solution of bromine (4 eq.) in DMF (0.5 ml/mmol). This reaction mixture was stirred at room temperature for about 4 hours, following which water was added and the mixture was extracted with dichloromethane (×3). The organic layer was washed with a saturated solution of Na2SO5, dried and evaporated to give a crude yellow oil. Purification by chromatography on silica gel (eluent: C6H12/EtOAc 9/1) afforded 3-brominated indole 11.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane (×3)
  3. washThe organic layer was washed with a saturated solution of Na2SO5
  4. customdried
  5. customevaporated
  6. customto give a crude yellow oil
  7. customPurification by chromatography on silica gel (eluent: C6H12/EtOAc 9/1)

Sources & evidence

ORD record
ord-d55ecee6241546d6bf04101ce3512fd9
Source dataset
uspto-grants-2009_05
Patent number
US07534809B2

Reaction notes

Loading…