Iodine → 3-Fluoro-2-iodoanisole

HRID 1420860ノート

反応式

HRID 1420860 の反応式
C([Li])CCC.[F:6][C:7]1[CH:8]=[C:9]([O:13][CH3:14])[CH:10]=[CH:11][CH:12]=1.[I:15]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1COCC1.CCOCC.O>[F:6][C:7]1[C:8]([I:15])=[C:9]([O:13][CH3:14])[CH:10]=[CH:11][CH:12]=1

参加物

8

反応物 4

HCID 807IodineHCID 99753-FluoroanisoleHCID 24477Sodium ThiosulfateHCID 178418339Butyllithium

生成物 1

HCID 27793163-Fluoro-2-iodoanisole収率 77%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

n-Butyllithium (1.6 M in hexanes, 26 mL, 42 mmol) was added dropwise to a stirred, cooled (-78° C.) solution of 3-fluoroanisole (5.0 g, 40 mmol) in THF (150 mL) and the mixture was stirred at -78° C. for 2.5 h. Iodine (11.1 g, 43 mmol) in THF (50 mL) was added dropwise and the mixture was allowed to warm to room temperature. Water (200 mL), saturated aqueous sodium thiosulfate (100 mL) and ether (300 mL) were added and the layers were separated. The aqueous layer was extracted with ether (200 mL), the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with hexane/EtOAc (99:1) to give the title compound as a pale yellow oil (7.65 g, 77%). 1H NMR (360 MHz, CDCl3) δ 7.27 (1H, dt, Jd 6.6 Hz, Jt 8.2 Hz), 6.71 (1H, t, J 8.2 Hz), 6.62 (1H, d, J 8.2 Hz), and 3.90 (3H, s).

後処理

  1. temperatureto warm to room temperature
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with ether (200 mL)
  4. dry with materialthe combined organic fractions were dried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with hexane/EtOAc (99:1)

出典と根拠

ORDレコード
ord-f2936a6600914951983351144ed4c9bc
出典データセット
uspto-grants-2000_06
特許番号
US06071927

反応ノート

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