(Diethylamino)sulfur trifluoride → 2-(3-Chlorophenyl)-2-fluoro-1-[4-(dimethylamino)phenyl]ethanone

HRID 1463375Notes

Reaction equation

HRID 1463375 reaction equation
C(N(S(F)(F)[F:7])CC)C.[Cl:10][C:11]1[CH:12]=[C:13]([CH:17](O)[C:18]([C:20]2[CH:25]=[CH:24][C:23]([N:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=2)=[O:19])[CH:14]=[CH:15][CH:16]=1>ClCCl>[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]([F:7])[C:18]([C:20]2[CH:25]=[CH:24][C:23]([N:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=2)=[O:19])[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 157284762-(3-Chlorophenyl)-2-hydroxy-1-[4-(dimethylamino)phenyl]ethanone

Product 1

HCID 157284782-(3-Chlorophenyl)-2-fluoro-1-[4-(dimethylamino)phenyl]ethanoneYield 9.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution 6.7 g of diethylaminosulfur trifluoride in 20 ml of dry dichloromethane was stirred at -78° C. under nitrogen as a solution of 12 g of 2-(3-chlorophenyl)-2-hydroxy-1-[4-(dimethylamino)phenyl]ethanone in 200 ml of dry dichloromethane was added dropwise. The mixture was warmed to room temperature and stirred for 72 hours. The mixture was poured into 200 ml of ice water and the layers separated. The organic layer was dried (Na2SO4), filtered, and evaporated. The residue was purifed by flash chromatography (8:1 hexane-ethyl acetate) and then recrystallized from ether-hexane to give 1.1 g of 2-(3-chlorophenyl)-2-fluoro-1-[4-(dimethylamino)phenyl]ethanone, mp 90°-92° C.

Workup

  1. additionwas added dropwise
  2. customthe layers separated
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customrecrystallized from ether-hexane

Sources & evidence

ORD record
ord-8c349d7e5a584ecc96d29656652a0f3b
Source dataset
uspto-grants-1994_04
Patent number
US05300527

Reaction notes

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