3,5-Dinitrobenzoyl chloride → [(1R)-1-[(2R)-2-(2,4-Difluorophenyl)-2-oxiranyl]ethyl]3,5-dinitrobenzoate

HRID 2395191Notes

Reaction equation

HRID 2395191 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([C@H:12]([OH:14])[CH3:13])[CH2:11][O:10]1.[N+:15]([C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([N+:27]([O-:29])=[O:28])[CH:26]=1)[C:21](Cl)=[O:22])([O-:17])=[O:16].C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@H:12]([O:14][C:21](=[O:22])[C:20]2[CH:19]=[C:18]([N+:15]([O-:17])=[O:16])[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=2)[CH3:13])[CH2:11][O:10]1

Participants

5

Reactant 3

HCID 74323,5-Dinitrobenzoyl chlorideHCID 8471TriethylamineHCID 15130436(1R)-1-[2-(2,4-difluorophenyl)-2-oxiranyl]ethanol

Product 1

HCID 10691998[(1R)-1-[(2R)-2-(2,4-Difluorophenyl)-2-oxiranyl]ethyl]3,5-dinitrobenzoateYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1R)-1-[2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (31.5 g) and 40 g of 3,5-dinitrobenzoyl chloride were dissolved in 500 ml of methylene chloride and, under ice-cooling, 24.1 ml of triethylamine was added dropwise thereinto. After the reaction mixture was stirred at room temperature for 3.5 hours, the resultant mixture was washed successively with 150 ml of water and with 150 ml of 5% aqueous solution of sodium bicarbonate. The resultant was dried over magnesium sulfate and concentrated under reduced pressure. The precipitated crystals were collected by filtration and washed with methylene chloride. The mother liquor and the washing were collected and the solvent was distilled off under reduced pressure. To the residue were added 25 ml of ethyl acetate and 300 ml of methanol, and the mixture was cooled with ice. The precipitated crystals were collected by filtration and recrystallized from a mixture of 25 ml of ethyl acetate and 250 ml of methanol to give 28.7 g of [(1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]3,5-dinitrobenzoate as colorless needles.

Workup

  1. temperaturecooling
  2. washthe resultant mixture was washed successively with 150 ml of water and with 150 ml of 5% aqueous solution of sodium bicarbonate
  3. dry with materialThe resultant was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with methylene chloride
  7. customThe mother liquor and the washing were collected
  8. distillationthe solvent was distilled off under reduced pressure
  9. additionTo the residue were added 25 ml of ethyl acetate and 300 ml of methanol
  10. temperaturethe mixture was cooled with ice
  11. filtrationThe precipitated crystals were collected by filtration
  12. customrecrystallized from a mixture of 25 ml of ethyl acetate and 250 ml of methanol

Sources & evidence

ORD record
ord-a7e04e9442654519a7dc53504446bc46
Source dataset
uspto-grants-1998_09
Patent number
US05814324

Reaction notes

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