1-Dodecanethiol → 1-Pentafluoroethylthiododecane

HRID 2285866Notes

Reaction equation

HRID 2285866 reaction equation
[CH2:1]([SH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.FC(F)(F)S([O-])(=O)=O.[F:37][C:38]([I+]C1C=CC=CC=1)([F:43])[C:39]([F:42])([F:41])[F:40]>C(Cl)Cl>[F:37][C:38]([F:43])([S:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:39]([F:42])([F:41])[F:40]

Participants

5

Reactant 3

HCID 81951-DodecanethiolHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 11488264Pentafluoroethylphenyliodonium trifluoromethanesulfonate

Product 1

HCID 128906271-Pentafluoroethylthiododecane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 ml of methylene chloride, 0.10 ml (0.42 mmol) of 1-dodecanethiol and 87 mg (0.42 mmol) of 2,6-di-tert-butyl-4-methylpyridine were added to a flask, and 198 mg (0.42 mmol) of pentafluoroethylphenyliodonium trifluoromethanesulfonate was added thereto in small portions while stirring at room temperature, followed by stirring at room temperature for 20 minutes. The resulting white precipitate was filtered and subjected to column chromatography of silica gel. Iodobenzene and the product was eluted with pentane and purified by gas chromatography to obtain 1-pentafluoroethylthiododecane as an oily substance. Yield, 87%.

Workup

  1. stirringby stirring at room temperature for 20 minutes
  2. filtrationThe resulting white precipitate was filtered
  3. washIodobenzene and the product was eluted with pentane
  4. custompurified by gas chromatography

Sources & evidence

ORD record
ord-23232a1b23dd44cd8fadf3905204f534
Source dataset
uspto-grants-1982_04
Patent number
US04324741

Reaction notes

Loading…