Trimethylsilyl iodide → 4-Iodophenylsulfur Pentafluoride

HRID 926100Notes

Reaction equation

HRID 926100 reaction equation
C[Si]([I:5])(C)C.F[B-](F)(F)F.[F:11][S:12]([F:24])([F:23])([F:22])([F:21])[C:13]1[CH:18]=[CH:17][C:16]([N+]#N)=[CH:15][CH:14]=1>>[I:5][C:16]1[CH:17]=[CH:18][C:13]([S:12]([F:24])([F:23])([F:22])([F:21])[F:11])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 1222352754-(Pentafluorosulfanyl)phenyldiazonium Tetrafluoroborate

Product 1

HCID 27791994-Iodophenylsulfur PentafluorideYield 40.3%

Procedure

(Bowden, et al., Tetrahedron 2000, 56, 3393-3408) Trimethylsilyl iodide (15.0 mg, 0.0750 mmol) was added to a solution of 1 (11.0 mg, 0.0346 mmol) in [BMIM][BF4] (67.6 mg). After stirring for 5 min the mixture was extracted with hexane (0.5 mL×3) and the combined extracts was evaporated to give pure 25b as a colorless oil (4.6 mg, 40%): MS (GC, EI): m/z=330 [M+], 311 [M+ F], 222, 96. 1H NMR (500 MHz, CDCl3): δ=7.82 (d, J=8.8 Hz, 2H), 7.48 (d, J=8.8 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3): δ=137.9 (2CH), 127.5 (2CH), 98.2 (C) ppm. 19F NMR (470 MHz, CDCl3): δ=83.5 (quint, J=151 Hz, 1 F), 62.8 (d, J=151 Hz, 4 F) ppm.

Workup

  1. extractionwas extracted with hexane (0.5 mL×3)
  2. customthe combined extracts was evaporated

Sources & evidence

ORD record
ord-67779f4ee8c349278d7b5fe5e724b2a3
Source dataset
uspto-grants-2016_03
Patent number
US09284336B1

Reaction notes

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