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

HRID 1457742ノート

反応式

HRID 1457742 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6aeac616ca6f45f3b54c334f677dc3ee
出典データセット
uspto-grants-1998_12
特許番号
US05849758

反応ノート

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