Bromine → HCID 52987842, compound

HRID 661109Notes

Reaction equation

HRID 661109 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-d7aaad54b4d342589b207f3694122f0f
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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