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

HRID 1531973Notes

Reaction equation

HRID 1531973 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-77529cf9a11c4c36aa5b3e7adbd83253
Source dataset
uspto-grants-2001_03
Patent number
US06200988B1

Reaction notes

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