Rac-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one → 3-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

HRID 2102734Notes

Reaction equation

HRID 2102734 reaction equation
C1C=C[NH+]=CC=1.[Br:7][Br-]Br.[Cl:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[C:16](=[O:20])[NH:17]2)=[CH:13][CH:12]=1>CC(O)(C)C.O>[Br:7][C:15]1([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[C:14]2[C:18](=[CH:19][C:11]([Cl:10])=[CH:12][CH:13]=2)[NH:17][C:16]1=[O:20]

Participants

4

Reactant 1

HCID 57507272Rac-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

Product 1

HCID 575072733-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-oneYield 100.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

Pyridinium bromide perbromide (0.659 g, 2.06 mmol) (Aldrich) was added in one portion to a solution of 6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (0.5 g, 1.72 mmol) (from Example 30b supra) in t-BuOH (16.2 mL) and H2O (74 uL) at room temperature with stirring. After stirring at room temperature for 4 hours, the crude was diluted with water, extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4. After filtration, the solvent was removed to obtain rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one as a pale yellow solid (yield: 0.64 g, 84%).

Workup

  1. stirringAfter stirring at room temperature for 4 hours
  2. extractionextracted with ethyl acetate three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-c2459d013aae42288a7ee09c4f75bfb0
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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