N-bromobutanimide → 5,6-Dibromoindolin-2-one

HRID 748512

Reaction equation

HRID 748512 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[Br:12]N1C(=O)CCC1=O>C(O)(=O)C>[Br:12][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[Br:1])[NH:8][C:7](=[O:11])[CH2:6]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27732896-bromo-2,3-dihydro-1H-indol-2-one

Product 1

HCID 688988855,6-Dibromoindolin-2-oneYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-Bromooxindole (0.168 g, 0.8 mmol) was dissolved in acetic acid (4 mL) and stirred for 5 min at room temperature. N-Bromosuccinimide (0.14 g, 0.8 mmol) was added and the yellow reaction mixture was stirred for 3 h at ambient temperature. The mixture was poured onto ice and the resulting precipitate was collected by filtration and dried in vacuo to give 0.192 g (83% yield) of the title compound as a white solid: 1H NMR (DMSO-d6, 400 MHz) δ 10.61 (s, 1 H), 7.60 (s, 1 H), 7.14 (s, 1 H), 3.52 (s, 2 H).

Workup

  1. stirringthe yellow reaction mixture was stirred for 3 h at ambient temperature
  2. additionThe mixture was poured onto ice
  3. filtrationthe resulting precipitate was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c6741f83f6e946e39933f32bd1d3aa49
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Linked notes

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