반응 #84346

반응 방정식

NH4Cl

4-Toluenesulfonyl chloride

6-fluoro-2,3-dihydro-1H-indole

→

title product

수율 61.2%

6-fluoro-1-tosylindoline

수율 61.2%

용매

THF

pyridine

반응 조건

후처리

1. 1
   기타Upon the completion of the reaction
2. 2
   온도the mixture was cooled to 0° C.
3. 3
   추출extracted with EtOAc (3×10 mL)
4. 4
   세척The combined extracts were sequentially washed with aq. sat. NH4Cl (3×10 mL), brine (10 mL)
5. 5
   건조dried (MgSO4)
6. 6
   농축The crude product was concentrated
7. 7
   기타dried over high vacuum

실험 절차

4-Toluenesulfonyl chloride (460 mg, 2.4 mmol) was slowly added to a solution of 6-fluoro-2,3-dihydro-1H-indole (220 mg, 1.6 mmol) in THF (6 mL) and pyridine (260 μL). The reaction mixture was stirred at room temperature overnight. Upon the completion of the reaction, the mixture was cooled to 0° C., neutralized with aq. sat. NH4Cl (10 mL) and extracted with EtOAc (3×10 mL). The combined extracts were sequentially washed with aq. sat. NH4Cl (3×10 mL), brine (10 mL) and dried (MgSO4). The crude product was concentrated and dried over high vacuum. Chromatography of the residue (EtOAc/hexanes=1/3) gave 283 mg (0.98 mmol) of the title product. Yield: 61%, colorless oil. 1H NMR (300 MHz, CDCl3): δ 7.67 (d, J=8.2 Hz, 2H), 7.35 (dd, J=10.0, 2.3 Hz, 1H), 7.23 (d, J=8.2 Hz, 2H), 6.97 (m, 1H), 6.62 (m, 1H), 3.90 (t, J=8.4 Hz, 2H), 2.84 (t, J=8.4 Hz, 2H), 2.35 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3): δ 162.5 (d, J=241.4 Hz), 144.5, 143.3 (d, J=11.7 Hz), 133.6, 129.8, 127.2, 127.0 (d, J=2.6 Hz), 125.7 (d, J=9.8 Hz), 110.0 (d, J=22.6 Hz), 102.8 (d, J=28.4 Hz), 50.7, 27.1, 21.5 ppm.

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