Chloroform → HCID 68854606, compound

HRID 494932Notes

Reaction equation

HRID 494932 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([O:12][CH3:13])[CH:11]=1)[C:8](=[O:14])[CH2:7][CH2:6]2.[Br:15]N1C(=O)CCC1=O.C(Cl)(Cl)Cl>ClCCl>[Br:15][C:4]1[C:3]([O:2][CH3:1])=[CH:11][C:10]([O:12][CH3:13])=[C:9]2[C:5]=1[CH2:6][CH2:7][C:8]2=[O:14]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 67184N-bromobutanimideHCID 43702075,7-Dimethoxy-indan-1-one

Product 1

HCID 68854606HCID 68854606, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

845 mg of 5,7-dimethoxyindan-1-one was dissolved in 40 ml of dichloromethane. Thereafter, 822 mg of N-bromosuccinimide was added to the reaction solution. After completion of the reaction, chloroform was added to the reaction solution. The organic layer was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. The residue was suspended in acetone, and the suspension was filtered, so as to obtain 1.03 g of 4-bromo-5,7-dimethoxyindan-1-one. The obtained product was suspended in a mixed solution consisting of 30 ml of methanol, 10 ml of tetrahydrofuran, and 20 ml of chloroform. Thereafter, 952 mg of methoxylamine hydrochloride and 935 mg of sodium acetate were added to the reaction solution, and the obtained mixture was stirred at room temperature. Approximately 4 hours later, 952 mg of methoxylamine hydrochloride and 935 mg of sodium acetate were further added to the reaction solution. After completion of the reaction, the reaction solution was concentrated. A saturated sodium bicarbonate aqueous solution and ethyl acetate were added to the resultant product, so as to separate an organic layer. The organic layer was washed with a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. The residue was suspended in t-butyl methyl ether, and the suspension was filtered, so as to obtain 896 mg of the subject compound.

Workup

  1. additionwas added to the reaction solution
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the drying agent
  5. filtrationby filtration
  6. concentrationthe organic layer was concentrated under a reduced pressure
  7. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-0e1f767fabed46e197fe45b85de2c330
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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