Dimethyl Disulfide → 2-Fluoro-6-(4'-trifluoromethylphenyl)-3-methylthio-pyridine

HRID 1457742Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:3]=1.[Li+].CC([N-]C(C)C)C.[CH3:26][S:27]SC>C1COCC1>[F:1][C:2]1[C:7]([S:27][CH3:26])=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:10][CH:9]=2)[N:3]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 2-fluoro-6-(4'-trifluoromethyl-phenyl)pyridine (2.4 g, 10 mmol, prepared according to example 17) in dry THF (35 mL) is added dropwise a solution of 2M LDA in THF (7.5 mL, 15 mmol) at -70° C. After 2 hours at -70° C. dimethyl disulfide (1.41 g, 15 mmol) is added and the reaction mixture is allowed to warm at -20 ° C. The mixture is hydrolysed and extracted with diethylether. After separation the organic layer is dried with anhydrous magnesium sulphate. The solvents are removed and the crude product is purified by flash column chromatography (silica gel). Elution with hexane/ethyl acetate (20/1 v/v) gives the title compound (1.2 g, 42%) with mp 70°-73° C.

Workup

extractionextracted with diethylether
customAfter separation the organic layer
dry with materialis dried with anhydrous magnesium sulphate
customThe solvents are removed
customthe crude product is purified by flash column chromatography (silica gel)
washElution with hexane/ethyl acetate (20/1 v/v)

Sources & evidence

ORD record: ord-6aeac616ca6f45f3b54c334f677dc3ee
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849758

Reaction notes

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