Water → 5-Bromo-2-oxindole

HRID 1990928Notes

Reaction equation

HRID 1990928 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].C([O-])(=O)C.[Na+].[Br:16]Br.O>C(Cl)(Cl)Cl.CCOC(C)=O>[Br:16][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:10])[CH2:3]2

Participants

7

Reactant 4

HCID 962WaterHCID 24408BromineHCID 321710OxindoleHCID 517045Sodium Acetate

Product 1

HCID 6111935-Bromo-2-oxindoleYield 97.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of oxindole (2.0 g, 15.0 mmol) and sodium acetate (2.1 g, 25.5 mmol) in CHCl3 (20 cm3) was treated with bromine (2.4 g, 15.0 mmol) in CHCl3 (10 cm3). After 30 min. the mixture was allowed to warm to RT and stirred for 1 h. The reaction mixture was diluted with EtOAc (500 cm3) and poured into water. The aqueous layer was extracted with EtOAc (×2), the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, brine, dried (MgSO4), and evaporated to give the title compound (3.1 g, 14.6 mmol, 96%) as an off-white solid which was used without further purification: m.p. 221-223° C.; 1H NMR (DMSO-d6) δ 3.51 (s, 2H), 6.76 (d, 1H, J=8.1 Hz), 7.33 (dd, 1H, J=8.1, 1.7 Hz), 7.37 (s, 1H), 10.49 (brs, 1H); 13C NMR (DMSO-d6) δ 36.10 (t), 111.21 (d), 113.16 (s), 127.54 (d), 128.3 (s), 130.40 (d), 143.34 (s), 176.24 (s); MS (EI) m/z 211, 213 (M)+.

Workup

  1. extractionThe aqueous layer was extracted with EtOAc (×2)
  2. washthe combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-50d9975f54eb49f1814f99fd19582441
Source dataset
uspto-grants-2010_01
Patent number
US07645761B2

Reaction notes

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