Methyl phenyl sulfoxide → Fluoromethyl phenyl sulfide

HRID 1777307Notes

Reaction equation

HRID 1777307 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.C(N(S(F)(F)[F:16])CC)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:16][CH2:1][S:2][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14516Methyl phenyl sulfoxideHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium Bicarbonate

Product 1

HCID 5314298Fluoromethyl phenyl sulfideYield 86%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of (methylsulfinyl)benzene (23.0 g, 164 mmol) in chloroform (80 mL) under argon at room temperature was added diethylaminosulfur trifluoride (43.0 mL, 328 mmol) dropwise and the reaction mixture was stirred for 2 days at this temperature then at 60° C. overnight. The mixture was added dropwise to a stirred solution of saturated aqueous sodium hydrogen carbonate at 0° C. then extracted 3 times with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated to give (fluoromethyl)(phenyl)sulfane (20.0 g, 86%) as a yellow oil.

Workup

  1. customat 60° C.
  2. customovernight
  3. extractionthen extracted 3 times with dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-28ee13892c5548468f0ba414a5345bb9
Source dataset
uspto-grants-2016_02
Patent number
US09266857B2

Reaction notes

Loading…