반응 #2325610

반응 방정식

water

dimethyl disulfide

189

2,7-dibromonaphthalene

n-BuLi

→

2-bromo-7-(methylsulfanyl)naphthalene

수율 82.0%

용매

THF

반응 조건

후처리

1. 1
   온도to warm to room temperature
2. 2
   기타The solvent was removed under reduced pressure
3. 3
   기타to give a residue that
4. 4
   기타the resulting solid was crystallised fom petroleum ether

실험 절차

A stirred solution of 189 (5.72 g, 20.0 mmol) in THF (80 mL) was treated dropwise at −78° C. with n-BuLi (2.5 M in hexanes, 8.40 mL, 21.0 mmol) under N2. The mixture was stirred at −78° C. for 20 min, then treated slowly with dimethyl disulfide (2.16 mL, 24 mmol) and allowed to warm to room temperature. The solvent was removed under reduced pressure to give a residue that was shaken with water, and the resulting solid was crystallised fom petroleum ether to give 2-bromo-7-(methylsulfanyl)naphthalene (199) (4.14 g, 82%): mp 80-81° C.; 1H NMR [(CD3)2SO] δ 8.11 (d, J=1.9 Hz, 1H), 7.86 (d, J=9.1 Hz, 1H), 7.83 (d, J=9.1 Hz, 1H), 7.71 (d, J=1.8 Hz, 1H), 7.54 (dd, J=8.72, 2.0 Hz, 1H), 7.44 (dd, J=8.6, 2.0 Hz, 1H), 2.58 (s, 3H). Anal. (C11H9BrS) C, H, S.

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