Water → HCID 58599386, compound

HRID 130487Notes

Reaction equation

HRID 130487 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19](=[O:21])[CH3:20])=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-:22].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.O>C1COCC1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19](=[O:21])[CH2:20][Br:22])=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 141129561-(1-Benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-ethanoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 58599386HCID 58599386, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ketone from step 1 (0.310 g, 1.02 mmol) was dissolved in THF (3 ml), and phenyltrimethylammonium tribromide (PTT) (0.386 g, 1.02 mmol) was added as a solid leaving an orange solution which began to deposit a white solid immediately. Stirring for 1.5 hours leaves a colorless mixture to which water (5 ml) was added. THF was then evaporated and the resulting aqueous mixture was extracted with ethyl acetate. Drying over Na2SO4 and evaporation leaves a white crystalline solid (85% desired mono-brominated material by LC-MS, 5% starting material, 10% dibrominated) suitable for the next step. LC-MS (ES+): 381, 379 m/e.

Workup

  1. customleaving an orange solution which
  2. additionwas added
  3. customTHF was then evaporated
  4. extractionthe resulting aqueous mixture was extracted with ethyl acetate
  5. dry with materialDrying over Na2SO4 and evaporation
  6. customleaves a white crystalline solid (85% desired mono-brominated material by LC-MS, 5%

Sources & evidence

ORD record
ord-08eda72d0acb4146a0fab8d82a3d9087
Source dataset
uspto-grants-2008_06
Patent number
US07381749B2

Reaction notes

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