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

HRID 1990936Notes

Reaction equation

HRID 1990936 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-55c8bf4cb0614f62a158216eae00d0c1
Source dataset
uspto-grants-2010_01
Patent number
US07645761B2

Reaction notes

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