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

HRID 1457742노트

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HRID 1457742 반응식
[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

참가 물질

5

반응물 3

HCID 12232Dimethyl DisulfideHCID 2724682Lithium diisopropylamideHCID 221006122-Fluoro-6-(4-(trifluoromethyl)phenyl)pyridine

생성물 1

HCID 221006092-Fluoro-6-(4'-trifluoromethylphenyl)-3-methylthio-pyridine수율 42%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-20 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-6aeac616ca6f45f3b54c334f677dc3ee
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849758

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