反応 #52853

反応方程式

triisopropylborate

6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene

n-BuLi

→

title compound

(5,6,7,8-Tetrahydro-5,5-dimethylnaphth-2-yl)boronic Acid

溶媒

HCl

toluene

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction stirred at room temperature for 12 h
2. 2
   抽出extracted with ether (2×)
3. 3
   洗浄The combined organic layer was washed with brine
4. 4
   乾燥dried over MgSO4
5. 5
   濃縮concentrated in vacuo
6. 6
   その他to give an oil
7. 7
   その他Recrystallization from hexane

実験手順

To a cold (−78° C.) solution of 2.02 g (8.4 mmol) of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene in 11.0 mL of toluene, was added 4.6 g (6.8 mL, 10.9 mmol, 1.6 M in hexane) of n-BuLi. The resulting solution was stirred at −78° C. for 45 min. and then 2.40 g (3.0 mL, 12.7 mmol) of triisopropylborate was dropwise added and the reaction stirred at room temperature for 12 h. The reaction was then diluted with 10% HCl, and extracted with ether (2×). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give an oil. Recrystallization from hexane afforded the title compound as a white solid.

出典