Dimethyl Sulfide → 5-Hydroxyoxindole

HRID 1615340Notes

Reaction equation

HRID 1615340 reaction equation
B(Br)(Br)Br.S(C)C.C[O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH2:13]2>ClCCCl>[OH:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[CH2:13]2

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 25134Boron tribromideHCID 15142865-Methoxyoxindole

Product 1

HCID 769555-HydroxyoxindoleYield 53%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

An oven-dried flask was charged with BBr3.SMe2 (2.80 g, 9.20 mmol) and 1,2-dichloroethane (15 mL). 5-Methoxyindolin-2-one (0.30 g, 1.84 mmol) was then added and the mixture was heated to reflux for 18 hours. The reaction was then cooled to room temperature and quenched with MeOH (1.0 mL). The mixture was then extracted into EtOAc washing with brine (3×). The organic layer was dried over MgSO4, filtered and the solvent removed in vacuo; the resulting residue was then purified by column chromatography (silica gel, 94:6 to 92:8, CH2Cl2/MeOH) to give 144 mg, 53% of a beige powder. MS ESI 149.9 [M+H]+, calcd for [C8H7NO2+H]+ 150.06

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 hours
  3. customquenched with MeOH (1.0 mL)
  4. extractionThe mixture was then extracted into EtOAc washing with brine (3×)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customthe resulting residue was then purified by column chromatography (silica gel, 94:6 to 92:8, CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-bb5f318afe4e430cb34d34c60c8023c4
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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