Iodine → 2-Fluoro-3-iodo-5-isopropylpyridine

HRID 2070931ノート

反応式

HRID 2070931 の反応式
C([N-]C(C)C)(C)C.[Li+].[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][N:11]=1.[I:19]I.O>C1COCC1>[F:9][C:10]1[C:15]([I:19])=[CH:14][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:12][N:11]=1

参加物

6

反応物 4

HCID 807IodineHCID 962WaterHCID 2724682Lithium diisopropylamideHCID 205879682-Fluoro-5-(1-methylethyl)pyridine

生成物 1

HCID 686713802-Fluoro-3-iodo-5-isopropylpyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a stirring solution of 9.2 mL of LDA (lithium diisopropylamide) (2.0M solution in THF/heptane/ethylbenzene) in 20 mL of THF at −78° C. was added 2-fluoro-5-isopropylpyridine in 40 mL of THF dropwise over a period of 20 min. After 30 min. 4.39 g (17.3 mmol) of iodine in 25 mL of THF was added. After 2 h at −78° C. with the light off, 20 mL of water was added, and the cold bath was removed. Water (80 mL) was added and 9 g of sodium thiosulfate was added in 3 portions. Diethyl ether was added, and the layers were separated. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (5% Et2O/hexanes) provided 1.83 g of 2-fluoro-3-iodo-5-isopropylpyridine with some impurity.

後処理

  1. customthe cold bath was removed
  2. additionWater (80 mL) was added
  3. addition9 g of sodium thiosulfate was added in 3 portions
  4. additionDiethyl ether was added
  5. customthe layers were separated
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by flash silica gel chromatography (5% Et2O/hexanes)

出典と根拠

ORDレコード
ord-de271da41fdf4a51a1c59305da350503
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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