Sodium Carbonate → 5-Bromo-3-methyl-indol-2-one

HRID 396223Notes

Reaction equation

HRID 396223 reaction equation
[Br:1]Br.[CH3:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:13].C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[Br:1][C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[C:4]([CH3:3])[C:5](=[O:13])[N:6]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24408BromineHCID 1509233-MethyloxindoleHCID 517045Sodium Acetate

Product 1

HCID 220193765-Bromo-3-methyl-indol-2-oneYield 93.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Under an atmosphere of nitrogen, bromine (0.96 g, 6.0 mmol) in acetic acid (5 cm3) was added drop wise to a solution of 3-methyl-2-indolinone (0.8749 g, 6.0 mmol) (Kende, et al, Synth. Commun., 12, 1, 1982) and sodium acetate (0.50 g, 6.0 mmol) in acetic acid (10 cm3). The reaction was stirred at room temperature for 3.5 h. Saturated sodium carbonate was added to quench the reaction. The water layer was extracted with EtOAc (×3), dried (MgSO4), filtered, and evaporated to give the title compound (1.26 g, 93%), Mp=119-120° C.; 1H NMR (DMSO) δ 1.32 (d, 3H, J=7.66 Hz), 3.45 (q, 1H, J=7.62 Hz), 6.77 (d, 1 H, J=8.23 Hz), 7.46 (s, 1H), 7.36-7.33 (m, 1H), 10.4 (s, 1H); IR (KBr) 3200, 1725 cm−; MS (EI) m/z 224/226 (M−H)−; CHN calculated for C9H8BrNO: C, 47.82; H, 3.57; N, 6.20; Found: C, 47.44; H, 3.42; N, 6.04.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe water layer was extracted with EtOAc (×3)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-cba352b66d984edbb8ebf937f8bb1c36
Source dataset
uspto-grants-2003_08
Patent number
US06608068B2

Reaction notes

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