Bromine → 5-Bromo-3-ethyl-1,3-dihydro-indol-2-one

HRID 396228Notes

Reaction equation

HRID 396228 reaction equation
[CH2:1]([CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:12])[CH3:2].C([O-])(=O)C.[Na+].[Br:18]Br>C(O)(=O)C.O>[Br:18][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4](=[O:12])[CH:3]2[CH2:1][CH3:2]

Participants

6

Reactant 3

HCID 24408BromineHCID 3473253-Ethylindolin-2-oneHCID 517045Sodium Acetate

Product 1

HCID 27718525-Bromo-3-ethyl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 3-ethyloxindole (6.0 g, 40 mmol) and sodium acetate (4 g, 48 mmol) in acetic acid (100 ml) was treated with bromine (6.4 g, 40 mmol). After 30 min. the mixture was diluted with water and extracted with EtOAc (2×); the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, and brine, dried (MgSO4) and evaporated to afford the crude product (9.2 g, 96%). A sample was recrystallized from EtOAc/hexane to obtain the subtitled compound, m.p. 130-132° C.; 1H-NMR (DMSO-d6) δ 0.74 (t, 3H, J=7.5 Hz), 1.8-2.0 (m, 2H), 3.45 (t, 1H, J=5.5 Hz,), 6.76 (d, 1H, J=8.35 Hz), 7.42 (m, 1H), 10.43 (s, 1H); MS (−ESI) m/z 238/240 (M−H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washthe combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto afford the crude product (9.2 g, 96%)
  6. customA sample was recrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-a44d07ae1abf4de7919c6ba98d660275
Source dataset
uspto-grants-2003_08
Patent number
US06608068B2

Reaction notes

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