Reaktion #158236

Reaktionsgleichung

NH4Cl

1,2-diiodo-4,5-dimethoxybenzene

isopropylmagnesium chloride

B(OiPr)3

→

pure product

Ausbeute 67.0%

2-iodo-4,5-dimethoxyphenylboronic acid

Ausbeute 67.0%

Lösungsmittel

—

mixture

Et2O

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   ExtraktionThe aqueous layer was extracted with Et2O (50 mL, 3 times)
3. 3
   Trocknendried over Na2SO4
4. 4
   Einengenconcentrated
5. 5
   workup.ADDITIONTo the concentrated sample, hexane was added
6. 6
   Sonstigethe resulting precipitate was isolated

Vorschrift

To a solution of 1,2-diiodo-4,5-dimethoxybenzene (Example 6(b), 2.0 g, 5.13 mmol) in 120 mL of a mixture of THF and Et2O (1:1) was added dropwise at −78° C. isopropylmagnesium chloride (2 M in THF, 2.67 mL, 5.39 mmol). After the mixture was stirred for 2 h at that temperature, B(OiPr)3 (10.89 ml, 15.39 mmol) was added. The solution was warmed to room temperature overnight; then a saturated solution of NH4Cl was added, and the resulting mixture was stirred for 30 min at room temperature. The aqueous layer was extracted with Et2O (50 mL, 3 times), dried over Na2SO4 and concentrated. To the concentrated sample, hexane was added and the resulting precipitate was isolated to give 1.05 g of the pure product (67%).

Quelle