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

HRID 852479Notes

Reaction equation

HRID 852479 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-bab245d2a70d4235a0f86c1ea004a9fb
Source dataset
uspto-grants-2007_08
Patent number
US07253203B2

Reaction notes

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