반응 #57546

반응 방정식

Sodium thiomethoxide

DMF

1-bromo-3-bromomethyl-benzene

→

1-bromo-3-methylsulfanylmethyl-benzene

수율 74.8%

용매

water

반응 조건

후처리

1. 1
   온도to warm to rt
2. 2
   추출extracted with EtOAc (3×20 mL)
3. 3
   건조dried with sodium sulfate
4. 4
   농축The solution was concentrated in vacuo
5. 5
   기타to yield the crude product, which
6. 6
   기타was then purified via flash chromatography (5% ethyl acetate—hexanes)

실험 절차

Sodium thiomethoxide (0.616 g, 8.8 mmol) was added to DMF (8 mL) and cooled to 0° C. To this solution was added 1-bromo-3-bromomethyl-benzene (2 g, 8 mmol). The mixture was allowed to warm to rt and stir for 18 h. The mixture was then poured into cold water (50 mL) and extracted with EtOAc (3×20 mL). The organics were combined and dried with sodium sulfate. The solution was concentrated in vacuo to yield the crude product, which was then purified via flash chromatography (5% ethyl acetate—hexanes) to yield 1.3 g (68.5%) of 1-bromo-3-methylsulfanylmethyl-benzene as a pure product. 1H-NMR (methylene chloride -d2) δ 7.48-7.47 (m, 1H), 7.392 (dt, J=7.9, 1.5 Hz, 1H), 7.28-7.207 (m, 2H), 3.64 (s, 2H), 1.99 (s, 3H); LC-MS RT: 3.70, [M+H]+: 354.1.

출처