(Diethylamino)sulfur trifluoride → HCID 67478733, compound

HRID 2089198Notes

Reaction equation

HRID 2089198 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10](O)[C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[C:4]#[N:5].CCN(S(F)(F)[F:22])CC>C(Cl)Cl>[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]([F:22])[C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 67478820HCID 67478820, compound

Product 1

HCID 67478733HCID 67478733, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Fluoro-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-benzonitrile (1 g, 4.56 mmol) in DCM (5 mL) was treated with DAST (Aldrich, 1.12 mL, 9.13 mmol) at −78° C. for 2 hours. The reaction was quenched with saturated NaHCO3 and extracted with DCM. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude material, purified by silica gel column (hexanes:ethyl acetate 4:1) to afford the title compound as colorless solid (1.01 g, 100%).

Workup

  1. customThe reaction was quenched with saturated NaHCO3
  2. extractionextracted with DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude material
  8. custompurified by silica gel column (hexanes:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-d49fd3b5cc6249c78ee6f888f852fc32
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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