Bromine → 1-Acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethylindoline

HRID 1107960Notes

Reaction equation

HRID 1107960 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[C:10]([CH3:13])[CH:11]=2)[CH:6]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:5]1)(=[O:3])[CH3:2].[Br:22]Br>CC(O)=O>[C:1]([N:4]1[C:12]2[C:7](=[C:8]([CH3:14])[C:9]([Br:22])=[C:10]([CH3:13])[CH:11]=2)[CH:6]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 222473291-Acetyl-3-(2-ethoxycarbonylethyl)-4,6-dimethylindoline

Product 1

HCID 222473121-Acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethylindoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Acetyl-3-(2-ethoxycarbonylethyl)-4,6-dimethylindoline (3.3 g) was dissolved in AcOH (30 ml) and Br2 (0.93 ml) was added, which was followed by stirring for 30 min. The reaction mixture was poured into ice water and precipitated crude crystals were collected by filtration. The obtained crystals were dissolved in CHCl3 (100 ml). After washing with water, the mixture was dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1) to give 3.0 g of 1-acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethylindoline.

Workup

  1. customprecipitated crude crystals
  2. filtrationwere collected by filtration
  3. dissolutionThe obtained crystals were dissolved in CHCl3 (100 ml)
  4. washAfter washing with water
  5. dry with materialthe mixture was dried over anhydrous sodium sulfate
  6. customCHCl3 was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1)

Sources & evidence

ORD record
ord-d2dbdd01f97a456daac93587aabc6ab7
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

Loading…