1,1-Dichloro-1-fluoromethanesulfenyl chloride → 1-(2,6-Dichloro-4-trifluoromethylphenyl)-2,5-dimethyl-3-(dichlorofluoromethylthio)pyrrole

HRID 1720461Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]1[CH3:19].[Cl:20][C:21]([Cl:25])([F:24])[S:22]Cl>ClCCl>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[C:14]([CH3:19])=[CH:15][C:16]([S:22][C:21]([Cl:25])([Cl:20])[F:24])=[C:17]1[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of 3.00 g (9.74 mmoles) of the 1-(2,6-dichloro-4-trifluoromethylphenyl)-2,5-dimethylpyrrole prepared above in 60 mL of dichloromethane was added dropwise 1.03 mL (1.67 g, 9.86 mmoles) of dichlorofluoromethanesulfenyl chloride in 5 mL of dichloromethane solution. The mixture was maintained at 0° C. for 3 hours and then washed with a saturated aqueous solution of NaHCO3. Removal of solvent under reduced pressure afforded a black off which was chromatographed on silica gel with a 1% EtOAc in hexane eluent to give 3.85 g (90%) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-2,5-dimethyl-3-(dichlorofluoromethylthio)pyrrole as a yellow off: 1H NMR (CDCl3): δ2.00 (s, 3H), 2.10 (s, 3H), 6.27 (s, 1H), 7.80 (s, 2H).

Workup

washwashed with a saturated aqueous solution of NaHCO3
customRemoval of solvent under reduced pressure
customafforded a black off which
customwas chromatographed on silica gel with a 1% EtOAc in hexane eluent

Sources & evidence

ORD record: ord-4823b68e3cc74b5e8fba5df2573b3a18
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05506260

Reaction notes

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