반응 #56928

반응 방정식

hydrochloric acid

sodium chloride

4-chloro-1-ethyl-2-iodo-benzene

isopropyl magnesium chloride

trimethyl borate

→

5-chloro-2-ethyl-phenyl boronic acid

수율 52.0%

용매

ethyl acetate

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred for 1.5 hours
2. 2
   건조The organic layer was dried over sodium sulfate
3. 3
   농축concentrated under reduced pressure
4. 4
   workup.ADDITIONThe residue was treated with hexane (50 ml)
5. 5
   여과the solid was filtered

실험 절차

To a solution of 4-chloro-1-ethyl-2-iodo-benzene (5 g, 18.8 mmol) in anhydrous tetrahydrofuran (40 ml), cooled to −30° C., was added isopropyl magnesium chloride (2 M in tetrahydrofuran, 10 ml, 20 mmol) dropwise. After stirring at −30° C. for 30 minutes, trimethyl borate (4.2 ml, 38 mmol) was added dropwise and the mixture was stirred for 1.5 hours. The mixture was treated with hydrochloric acid (1 M, 25 ml), ethyl acetate (100 ml), and saturated aqueous sodium chloride solution (100 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was treated with hexane (50 ml) and the solid was filtered to afford 5-chloro-2-ethyl-phenyl boronic acid (1.8 g, 52% yield) as a white powder.

출처