Bromine → HCID 66788818, compound

HRID 1623548Notes

Reaction equation

HRID 1623548 reaction equation
[CH:1]1([C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[C:5]=2[CH2:6][C:7](=[O:14])[N:8]3[CH3:13])[CH2:3][CH2:2]1.[Br-:15].[K+].BrBr>O.ClCCl.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>[Br:15][C:12]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:13])[C:7](=[O:14])[CH2:6]2

Participants

8

Reactant 3

HCID 24408BromineHCID 253877Potassium BromideHCID 66788042HCID 66788042, compound2×

Product 1

HCID 66788818HCID 66788818, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

Water (14 mL) was added to 4-cyclopropyl-1-methyl-1,3-dihydro-indol-2-one (0.74 g, 3.94 mmol) and the resulting mixture was placed at 70° C. In a separate flask potassium bromide (1.03 g, 8.7 mmol) in water (14 was treated with bromine (0.225 mL, 4.3 mmol), the resulting orange solution was added dropwise to the 4-cyclopropyl-1-methyl-1,3-dihydro-indol-2-one mixture over ca. 10 minutes. The resulting heterogeneous mixture was permitted to stir at 70° C. for an additional hour and then cooled to room temperature. The reaction was then diluted with dichloromethane and saturated aqueous sodium bicarbonate. The solution was then further diluted with saturated aqueous sodium thiosulfate. The layers were separated and the aqueous layer eras extracted two additional times with dichloromethane. The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was preadsorbed onto silica gel and purified by silica gel flash chromatography (ethyl acetate-heptane 0 to 50%) to provide 5-bromo-4-cyclopropyl-1-methyl-1,3-dihydro-indol-2-one; MS: (ES+) m/z 266.2 (M+H)+.

Workup

  1. customwas placed at 70° C
  2. temperaturecooled to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer eras extracted two additional times with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel flash chromatography (ethyl acetate-heptane 0 to 50%)

Sources & evidence

ORD record
ord-c4ae6591230f40b9a9b0d2e338d72f1d
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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