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

HRID 990642Notes

Reaction equation

HRID 990642 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 title 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-52bf1a74a92e4dc0993e35d6947ac477
Source dataset
uspto-grants-2002_10
Patent number
US06462032B1

Reaction notes

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