1-Bromo-2-Chloroethane → HCID 11770201, compound

HRID 1276329Notes

Reaction equation

HRID 1276329 reaction equation
[F: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].[H-].[Na+].Br[CH2:16][CH2:17][Cl:18]>CN(C)C=O>[Cl:18][CH2:17][CH2:16][N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[C:5](=[O:12])[C:6]1=[O:11]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 2365665-Fluoroisatin

Product 1

HCID 11770201HCID 11770201, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Fluoro-1H-indole-2,3-dione was dissolved in dimethylformamide. Sodium hydride (60% dispersion in mineral oil)(1.2 equivalents) was added in portions with stirring and cooling (ice-water bath) and the mixture was stirred until gas evolution ceased. 1-Bromo-2-chloroethane (1.2 equivalents) was added dropwise. The mixture was stirred at room temperature for 24 hours and then quenched into water and extracted into chloroform. The combined organic phases were washed with water, dried (MgSO4), filtered and concentrated under reduced pressure. The resulting oil was purified by chromatography on silica gel, eluent chloroform, to give 1-(2-chloro-1-ethyl)-5-fluoro-1H-indole-2,3-dione as a red solid.

Workup

  1. stirringthe mixture was stirred until gas evolution
  2. stirringThe mixture was stirred at room temperature for 24 hours
  3. customquenched into water
  4. extractionextracted into chloroform
  5. washThe combined organic phases were washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting oil was purified by chromatography on silica gel, eluent chloroform

Sources & evidence

ORD record
ord-2821e83b547948aa9d2f201298cb912a
Source dataset
uspto-grants-2000_12
Patent number
US06166040

Reaction notes

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