Reaktion #366244

Reaktionsgleichung

triethyl borate

3-isopropoxy-4-bromotoluene

tetrahydrofuran

butyl lithium

→

2-Isopropoxy-4-methylphenylboronic Acid

Lösungsmittel

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 125 mL 3N round-bottomed flask equipped with N2 inlet
2. 2
   workup.STIRRINGby stirring for 5 minutes at −70° C.
3. 3
   workup.STIRRINGstirring at room temperature for 24 hours
4. 4
   SonstigeThe reaction was quenched with 1 N aqueous hydrochloric acid
5. 5
   Extraktionextracted into ethyl acetate
6. 6
   WaschenThe organic layer was washed with water and brine
7. 7
   Trocknendried over sodium sulfate
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe residue was triturated with hexane to a white solid, 1.7 g (56%)

Vorschrift

To a 125 mL 3N round-bottomed flask equipped with N2 inlet and septum were added 3.59 g (15.7 mmol) 3-isopropoxy-4-bromotoluene and 30 mL dry tetrahydrofuran. The solution was cooled to −70° C. and 7.5 mL (18.8 mmol) of a 2.5 M solution of butyl lithium in hexane was added over 5 minutes, and the solution stirred 5 minutes at −70° C. Then 3.2 mL (18.8 mmol) triethyl borate was added, followed by stirring for 5 minutes at −70° C. and then stirring at room temperature for 24 hours. The reaction was quenched with 1 N aqueous hydrochloric acid and extracted into ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, and evaporated. The residue was triturated with hexane to a white solid, 1.7 g (56%).

Quelle