Reaction #1476

Reaction equation

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

Solvents

HCl

toluene

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction stirred at room temperature for 12 h
2. 2
   Extractionextracted with ether (2×)
3. 3
   WashThe combined organic layer was washed with brine
4. 4
   Dryingdried over MgSO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   Otherto give an oil
7. 7
   OtherRecrystallization from hexane

Procedure

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, 1.6M 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.

Source