반응 #1966100

반응 방정식

1-chloro-2-(2,2-diethoxyethylsulfanyl)benzene

→

7-chlorobenzo[b]thiophene

수율 67.5%

용매

toluene

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도at reflux for 4 h.
3. 3
   추출extracted with toluene
4. 4
   세척The combined toluene extracts were washed with aqueous sodium bicarbonate
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타evaporated under reduced pressure
7. 7
   기타to yield the crude product
8. 8
   기타This material was purified by chromatography over silica gel eluting with hexane

실험 절차

To a solution of 1-chloro-2-(2,2-diethoxyethylsulfanyl)benzene (3.95 g, 15.14 mmol) in toluene (40 mL) was added polyphosphoric acid (15 g, 137.5 mmol). The mixture was heated at reflux for 4 h. then was poured in to ice water, stirred for 30 min and extracted with toluene. The combined toluene extracts were washed with aqueous sodium bicarbonate followed by brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to yield the crude product. This material was purified by chromatography over silica gel eluting with hexane to afford pure 7-chlorobenzo[b]thiophene (1.72 g, 67.5%). 1H NMR (400 MHz, CDCl3) δ=7.13-7.30 (m, 3H), 7.38 (d, J=5.31 Hz, 1H), 7.62 (dd, J=7.33, 1.52 Hz, 1H); MS (ES+): m/z 169.06 [MH+].

출처