Dichloromethane → HCID 22004835, compound

HRID 324613Notes

Reaction equation

HRID 324613 reaction equation
B(Br)(Br)Br.ClCCl.[F:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18]C)[CH:14]([CH2:20][CH2:21][NH:22][C:23](=[O:26])[CH2:24][CH3:25])[CH2:13][CH2:12]2>O>[F:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[OH:18])[CH:14]([CH2:20][CH2:21][NH:22][C:23](=[O:26])[CH2:24][CH3:25])[CH2:13][CH2:12]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 22004861HCID 22004861, compound

Product 1

HCID 22004835HCID 22004835, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Boron tribromide (7.9 g, 31.5 mmols) was gradually and dropwise added to a dichloromethane (100 ml) solution of N-[2-(5-fluoro-6-methoxyindan-1-yl)ethyl]propionamide (4.18 g, 15.8 mmols) while cooling with ice. After having been stirred for 2 hours while still cooling with ice, the reaction mixture was poured into water containing ice and then stirred at room temperature for 3 hours, and the organic substance was extracted with ethyl acetate. The extract was washed with a saturated saline solution and water and then dried with anhydrous magnesium sulfate, and the solvent was removed through distillation under reduced pressure. The resulting residue was purified through silica-gel column chromatography (ethyl acetate/hexane=9/1) to obtain 3.68 g (yield: 93%) of the target compound.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile still cooling with ice
  3. additioncontaining ice
  4. stirringstirred at room temperature for 3 hours
  5. extractionthe organic substance was extracted with ethyl acetate
  6. washThe extract was washed with a saturated saline solution and water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customthe solvent was removed through distillation under reduced pressure
  9. customThe resulting residue was purified through silica-gel column chromatography (ethyl acetate/hexane=9/1)

Sources & evidence

ORD record
ord-f1adc248d2e641fe9e218310a47ffd21
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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