Iodine → 3-Fluoro-2-iodoanisole

HRID 1420860노트

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HRID 1420860 반응식
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

참가 물질

8

반응물 4

HCID 807IodineHCID 99753-FluoroanisoleHCID 24477Sodium ThiosulfateHCID 178418339Butyllithium

생성물 1

HCID 27793163-Fluoro-2-iodoanisole수율 77%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f2936a6600914951983351144ed4c9bc
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06071927

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