Iodine → 6-Bromo-2-chloro-3-iodoquinoline

HRID 1028932ノート

反応式

HRID 1028932 の反応式
[Li]CCCC.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([Cl:17])[CH:11]=[CH:10]2.[I:18]I.C1COCC1.O>C1COCC1.CCCCCC.C(OCC)C.O>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([Cl:17])[C:11]([I:18])=[CH:10]2

参加物

9

反応物 4

HCID 807IodineHCID 128940866-Bromo-2-chloroquinolineHCID 21881883Oxolane--water (1/1)HCID 178418339Butyllithium

生成物 1

HCID 866768376-Bromo-2-chloro-3-iodoquinoline

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

To a solution of THF (50 mL) and DIPA (1.8 mL, 12.37 mmol) at −70° C. was added n-BuLi (7.7 mL, 12.4 mmol). The mixture was allowed to stir at 0° C. for 1 h. Slow addition of 6-bromo-2-chloroquinoline (3.0 g, 12.4 mmol) in THF (50 mL) was achieved at −75° C. and the mixture was stirred at this temperature for 2 h. Iodine (3.1 g, 12.4 mmol) in 10 ml of THF was then slowly added and the reaction mixture was allowed to stir at −75° C. for 2 h before hydrolysis by THF/water (20% v/v). Water and diethyl ether were added at −10° C. and the reaction mixture was extracted with ether. The organic layer was washed with sodium thiosulfate and water, dried over MgSO4 and concentrated in vacuo to give a yellow solid which was slurried with hexane and filtered to give 6-bromo-2-chloro-3-iodoquinoline as a tan solid.

後処理

  1. customwas achieved at −75° C.
  2. stirringthe mixture was stirred at this temperature for 2 h
  3. extractionthe reaction mixture was extracted with ether
  4. washThe organic layer was washed with sodium thiosulfate and water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give a yellow solid which
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-70467365e91d4518bf222a527cb517e8
出典データセット
uspto-grants-2014_05
特許番号
US08735384B2

反応ノート

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