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

HRID 1084919Notes

Reaction equation

HRID 1084919 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]ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution 6.7 g 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 purified 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. customThe residue was purified by flash chromatography (8:1 hexane-ethyl acetate)
  7. customrecrystallized from ether-hexane

Sources & evidence

ORD record
ord-348d631e72154daf9fb61bb003ff4e2a
Source dataset
uspto-grants-1991_04
Patent number
US05006563

Reaction notes

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