Naphthalene → (Fluoromethyl)(naphthalen-2-yl)(p-tolyl)sulfonium tetrafluoroborate

HRID 926952Notes

Reaction equation

HRID 926952 reaction equation
[F:1][CH2:2][S:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=O.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[H+].[B-:38]([F:42])([F:41])([F:40])[F:39]>C(OCC)C>[F:39][B-:38]([F:42])([F:41])[F:40].[F:1][CH2:2][S+:3]([C:14]1[CH:13]=[CH:12][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1)[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 931NaphthaleneHCID 28118Tetrafluoroboric acidHCID 67749Trifluoromethanesulfonic anhydrideHCID 3251341-(Fluoromethylsulfinyl)-4-methylbenzene

Product 1

HCID 131735035(Fluoromethyl)(naphthalen-2-yl)(p-tolyl)sulfonium tetrafluoroborate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1-((Fluoromethyl)sulfinyl)-4-methylbenzene (481 mg, 2.79 mmol) of example 5 was dissolved in dry diethyl ether (15 mL) under argon atmosphere. Naphthalene (393.8 mg, 1.1 eq) was added to the previous solution and then the mixture was cooled to a temperature below −50° C. After stabilizing the temperature below −50° C., trifluoromethanesulfonic anhydride (0.47 mL, 1 eq) was added slowly maintaining the same temperature. The mixture was stirred, at the same temperature, until the reaction was complete. HBF4 in diethyl ether (54%, 0.77 mL, 2 eq) was added. The resulting suspension was stirred for 30 minutes. The precipitate tetrafluoroborate salt was isolated by filtration and washed with diethyl ether at 0° C. The desired product was obtained as a yellow oily solid (1.873 g) after heating at room temperature.

Workup

  1. temperaturethe mixture was cooled to a temperature below −50° C
  2. additionwas added slowly
  3. temperaturemaintaining the same temperature
  4. stirringThe resulting suspension was stirred for 30 minutes

Sources & evidence

ORD record
ord-de18d352cd6c4f4cb27f0451cd61bc26
Source dataset
uspto-grants-2016_03
Patent number
US09290446B2

Reaction notes

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