Methanol → 2-Bromo-1-[3-(cyclopentyloxy)-4-methoxyphenyl]ethan-1-one

HRID 2097533Notes

Reaction equation

HRID 2097533 reaction equation
CO.[CH:3]1([O:8][C:9]2[CH:10]=[C:11]([C:17](=[O:19])[CH3:18])[CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:7][CH2:6][CH2:5][CH2:4]1.[Br-:20].[Br-].[Br-].C[N+](C)(C)C1C=CC=CC=1.C[N+](C1C=CC=CC=1)(C)C.C[N+](C1C=CC=CC=1)(C)C.C(=O)([O-])O.[Na+]>O>[Br:20][CH2:18][C:17]([C:11]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:9]([O:8][CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7]2)[CH:10]=1)=[O:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 117465791-(3-(Cyclopentyloxy)-4-methoxyphenyl)ethanoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 544385052-Bromo-1-[3-(cyclopentyloxy)-4-methoxyphenyl]ethan-1-oneYield 41.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 200 ml of methanol solution containing 11.6 g (49.5 mmol) of 1-(3-cyclopentoxy-4-methoxyphenyl)ethanone (see Bioorg. Med. Chem. Lett. 2003, 13, 2355) was added 20.47 g (54.5 mmol) of trimethylphenylammonium tribromide at room temperature, and the mixture was stirred at room temperature for 40 minutes. After completion of the reaction, water was added to the reaction mixture, and the mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate and then extracted with chloroform. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. To the obtained concentrate was added 50 ml of a mixed solvent (diisopropyl ether/hexane=1/2 (V/V)), and precipitated solid was collected by filtration. The obtained solid was washed with diisopropyl ether, and dried under reduced pressure to obtain 6.47 g of the title compound as a white solid. (Yield: 41%)

Workup

  1. additionwas added to the reaction mixture
  2. extractionextracted with chloroform
  3. customThe organic layer after separation
  4. washwas washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. concentrationTo the obtained concentrate
  8. additionwas added 50 ml of a mixed solvent (diisopropyl ether/hexane=1/2 (V/V))
  9. customprecipitated solid
  10. filtrationwas collected by filtration
  11. washThe obtained solid was washed with diisopropyl ether
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-24ecabb0cb184d8087b4dfdf88b4c9e4
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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