Bromine → HCID 52987842, compound

HRID 2109780Notes

Reaction equation

HRID 2109780 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2.[Br:12]Br.[K+].[Br-]>O>[Br:12][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([F:1])[CH:3]=1)[NH:9][C:8](=[O:11])[CH2:7]2

Participants

5

Reactant 3

HCID 24408BromineHCID 253877Potassium BromideHCID 37343717-Fluoro-2,3-dihydro-1h-indol-2-one

Product 1

HCID 52987842HCID 52987842, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

7-Fluoroindolin-2-one (800 mg, 5293 μmol) was taken up in 30 mL of boiling water. Br2 (273 μL, 5293 μmol) and KBr (1260 mg, 10586 μmol) were added dropwise in 5 mL of water over 10 minutes. A white precipitate began to form as the solution was added. The mixture was stirred for 20 minutes. The mixture was then chilled in an ice bath for 30 minutes, washed with 30 mL of a saturated NaHCO3 solution and extracted twice with 50 mL of EtOAc. The organic layers were concentrated and purified with silica gel column chromatography, eluting with 0-35% EtOAc/hexane to give 5-bromo-7-fluoroindolin-2-one (913 mg, 75% yield). MS m/z: 230 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 3.58 (s, 2H), 7.20 (dd, J=10.07, 0.88 Hz, 2H), 7.63 (s, 1H).

Workup

  1. customto form as the solution
  2. additionwas added
  3. temperatureThe mixture was then chilled in an ice bath for 30 minutes
  4. washwashed with 30 mL of a saturated NaHCO3 solution
  5. extractionextracted twice with 50 mL of EtOAc
  6. concentrationThe organic layers were concentrated
  7. custompurified with silica gel column chromatography
  8. washeluting with 0-35% EtOAc/hexane

Sources & evidence

ORD record
ord-f1c8c8578f0a4b84bf5a1601634ba85d
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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