6-Nitro-1H-indole → 3-Bromo-6-nitro-1H-indole

HRID 2079876Notes

Reaction equation

HRID 2079876 reaction equation
[Br:1]NC(=O)CCC(N)=O.[N+:10]([C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[CH:18][NH:19]2)=[CH:15][CH:14]=1)([O-:12])=[O:11]>O1CCCC1>[Br:1][C:17]1[C:16]2[C:20](=[CH:21][C:13]([N+:10]([O-:12])=[O:11])=[CH:14][CH:15]=2)[NH:19][CH:18]=1

Participants

4

Reactant 2

HCID 785026-Nitro-1H-indoleHCID 9834204N-Bromosuccinamide

Product 1

HCID 147079343-Bromo-6-nitro-1H-indoleYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add N-bromosuccinamide (NBS) to 6-nitroindole 1 (22.72 g, 140.12 mmol) dissolved in tetrahydrofuran (600 mL) and allow the resulting mixture to stir for 18 hours. Quench the reaction mixture with saturated aqueous sodium thiosulfate solution (600 mL), dilute with ethyl acetate (EtOAc) (600 mL), and separate the layers. Sequentially, wash the organic layer with saturated aqueous sodium bisulfate (100 mL), saturated aqueous sodium bicarbonate (100 mL), water (100 mL), and brine (100 mL). Dry the resulting organic layer over Na2SO4 and filter. Concentrate the filtrate to give a yellow solid. Recrystallize the solid from dichloromethane and hexane to give 29.21 g of the title compound (86%). LRMS (API ES+)=263.0 (M+Na).

Workup

  1. customQuench the reaction mixture with saturated aqueous sodium thiosulfate solution (600 mL)
  2. additiondilute with ethyl acetate (EtOAc) (600 mL)
  3. customseparate the layers
  4. washSequentially, wash the organic layer with saturated aqueous sodium bisulfate (100 mL), saturated aqueous sodium bicarbonate (100 mL), water (100 mL), and brine (100 mL)
  5. dry with materialDry the resulting organic layer over Na2SO4
  6. filtrationfilter
  7. concentrationConcentrate the filtrate
  8. customto give a yellow solid
  9. customRecrystallize the solid from dichloromethane and hexane

Sources & evidence

ORD record
ord-e9af0bf0d4e54f8588dc3affc21c2382
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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