Reaction #2487420

Reaction equation

1,4-dibromonaphthalene

n-butyllithium

chlorotrimethylsilane

EtOH

→

(4-bromonaphth-1-yl)trimethylsilane

Solvents

THF

THF

water

Conditions

Workup

1. 1
   workup.ADDITIONare subsequently slowly added at this temperature
2. 2
   workup.ADDITIONis added to the solution
3. 3
   Otherobtained in this way
4. 4
   Temperaturethe mixture is slowly warmed to room temperature
5. 5
   Otherthe organic phase is separated off
6. 6
   Dryingdried over magnesium sulfate
7. 7
   Otherevaporated
8. 8
   OtherThe oil obtained in this way
9. 9
   workup.DISTILLATIONis distilled at 115-135° C.
10. 10
    Other1.7 mbar, giving 80 g (286 mmol) (corresponding to 88% of theory) of the product

Procedure

A solution of 114.38 g (400 mmol) of 1,4-dibromonaphthalene and 1 l of THF (absolute) is cooled to −78° C. under protective gas, 160 ml (400 mmol) of n-butyllithium (2.5M in n-hexane) are subsequently slowly added at this temperature, and the mixture is stirred at −78° C. for a further 30 h. A mixture of 52.3 ml (400 mmol) of chlorotrimethylsilane in 200 ml of THF (absolute) is added to the solution obtained in this way, and the mixture is slowly warmed to room temperature. After addition of 150 ml of EtOH and subsequently 300 ml of water, the organic phase is separated off, dried over magnesium sulfate and evaporated. The oil obtained in this way is distilled at 115-135° C. and 1.7 mbar, giving 80 g (286 mmol) (corresponding to 88% of theory) of the product having a purity of greater than 99.0% according to HPLC.

Source