5-Bromoisatin → 5-Bromo-3-hydroxy-3-prop-1-ynyl-1,3-dihydroindol-2-one

HRID 990647Notes

Reaction equation

HRID 990647 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].[C:13]([Mg]Br)#[C:14][CH3:15].[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([OH:12])[C:13]#[C:14][CH3:15]

Participants

5

Reactant 3

HCID 68895-BromoisatinHCID 25517Ammonium ChlorideHCID 178419101HCID 178419101, compound

Product 1

HCID 120859385-Bromo-3-hydroxy-3-prop-1-ynyl-1,3-dihydroindol-2-oneYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromoisatin (2.5 g, 11 mmol) in dry THF (100 cm3) at −10° C. under a nitrogen atmosphere was added 1-propynylmagnesium bromide (0.5 M in THF, 47 cm3, 23.5 mmol). After 1 h, the mixture was poured into saturated ammonium chloride and extracted with EtOAc (×3), washed with brine, dried (MgSO4) and evaporated to afford 5-bromo-3-hydroxy-3-prop-1-ynyl-1,3-dihydroindol-2-one (2.83 g, 10.6 mmol, 97%) which was used without further purification: (CDCl3) δ 1.83 (s, 3H), 6.79 (d, 1H, J=8.0 Hz), 6.90 (s, 1H), 7.41-7.44 (m, 2H), 10.59 (s, 1H); MS ((−) ESI) m/z 264 (M−H)−.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-714816f29e2b44d399b2ea76ba7ae708
Source dataset
uspto-grants-2002_10
Patent number
US06462032B1

Reaction notes

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