Reaktion #74463

Reaktionsgleichung

5-bromo-2-chlorobenzyl alcohol

5-Bromo-2-chlorobenzyl alcohol

triisopropylsilyl chloride

→

title compound

Ausbeute 95.0%

(5-Bromo-2-chlorobenzyloxy)triisopropylsilane

Ausbeute 95.0%

Lösungsmittel

N,N-dimethylformamide

ammonium chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe organic layer was washed with water
3. 3
   Trocknenbrine, dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe crude residue was purified on Biotage® purification apparatus (silica gel, 3 to 10% ethyl acetate in hexanes)

Vorschrift

To a solution of 5-bromo-2-chlorobenzyl alcohol (425 mmol) from Step 2 in N,N-dimethylformamide (400 mL) was added imidazle (58 g, 850 mmol), 4-(dimethylamino)pyridine (2.6 g, 21 mmol), and triisopropylsilyl chloride (136 mL, 638 mmol). The resulting solution was stirred at ambient temperature for 15 h, diluted with a saturated ammonium chloride and extracted with ethyl acetate. The organic layer was washed with water then brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus (silica gel, 3 to 10% ethyl acetate in hexanes) to yield the title compound (152 g, 403 mmol, 95%) as a colorless oil.

Quelle