Potassium Carbonate → Pyridine, 2,6-dichloro-4-[1-(trifluoromethyl)ethenyl]-

HRID 2172529ノート

反応式

HRID 2172529 の反応式
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([Cl:9])[N:3]=1.[F:10][C:11]([F:18])([F:17])[C:12](B(O)O)=[CH2:13].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:12]([C:11]([F:18])([F:17])[F:10])=[CH2:13])[CH:5]=[C:4]([Cl:9])[N:3]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 2782677(3,3,3-Trifluoroprop-1-en-2-yl)boronic acidHCID 117373932,6-Dichloro-4-iodopyridine

生成物 1

HCID 86664620Pyridine, 2,6-dichloro-4-[1-(trifluoromethyl)ethenyl]-収率 91.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

2,6-dichloro-4-iodopyridine (0.87 g), (3,3,3-trifluoroprop-1-en-2-yl)boronic acid (purity: 65%, 0.75 g) and potassium carbonate (0.96 g) were dissolved in the mixed solvent of THF and water, which was then degassed three times. To the solution was added dichlorobis(triphenylphosphine) palladium (II) (0.04 g), and the mixture was heated to reflux for 3 hours under argon atmosphere. The mixture was cooled to room temperature and then poured into water, which was then extracted twice with hexane. The organic layer was combined, which was then washed with water and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under reduced pressure, and the residue was then purified by silica gel chromatography to obtain 2,6-dichloro-4-(3,3,3-trifluoroprop-1-en-2-yl)pyridine (0.70 g) at a yield of 82%.

後処理

  1. customwas then degassed three times
  2. additionTo the solution was added dichlorobis(triphenylphosphine) palladium (II) (0.04 g)
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 3 hours under argon atmosphere
  5. additionpoured into water, which
  6. extractionwas then extracted twice with hexane
  7. washwhich was then washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter the drying agent was filtered off
  10. distillationthe solvent was distilled away under reduced pressure
  11. customthe residue was then purified by silica gel chromatography

出典と根拠

ORDレコード
ord-b15e5d2bb25145a284be352f3d6abec1
出典データセット
uspto-grants-2015_06
特許番号
US09055749B2

反応ノート

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