반응 #2163734

반응 방정식

potassium carbonate

2-chlorobenzenethiol

2-bromo-1,1-diethoxyethane

→

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

수율 80.0%

용매

acetone

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도at reflux for 3 h.
3. 3
   여과filtered
4. 4
   기타the filtrate evaporated under reduced pressure
5. 5
   기타to yield the crude product
6. 6
   기타This material was purified by chromatography over silica gel eluting with ethyl acetate in hexanes (0→2%)

실험 절차

To a solution of 2-chlorobenzenethiol (5.0 g, 34.5 mmol) in acetone (35 mL) was added 2-bromo-1,1-diethoxyethane (7.15 g, 36.3 mmol) followed by potassium carbonate (9.55 g, 69.1 mmol). The mixture was heated at reflux for 3 h. then cooled to rt, filtered and the filtrate evaporated under reduced pressure to yield the crude product. This material was purified by chromatography over silica gel eluting with ethyl acetate in hexanes (0→2%) to afford pure 1-chloro-2-(2,2-diethoxyethylsulfanyl)benzene (7.3, 80%). 1H NMR (400 MHz, CDCl3) δ=1.20 (t, J=7.07 Hz, 6H), 3.15 (d, J=5.56 Hz, 2H), 3.51-3.61 (m, 2H), 3.63-3.74 (m, 2H), 4.69 (t, J=5.56 Hz, 1H), 7.12 (td, J=7.58, 1.52 Hz, 1H), 7.20 (td, J=7.58, 1.52 Hz, 1H), 7.36 (dd J=−7.83, 1.52 Hz, 1H), 7.39 (dd, J=8.08, 1.52 Hz, 1H); MS (ES+): m/z 187.17 [M-74].

출처