반응 #74463

반응 방정식

5-bromo-2-chlorobenzyl alcohol

5-Bromo-2-chlorobenzyl alcohol

triisopropylsilyl chloride

→

title compound

수율 95.0%

(5-Bromo-2-chlorobenzyloxy)triisopropylsilane

수율 95.0%

용매

N,N-dimethylformamide

ammonium chloride

반응 조건

후처리

1. 1
   추출extracted with ethyl acetate
2. 2
   세척The organic layer was washed with water
3. 3
   건조brine, dried over magnesium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The crude residue was purified on Biotage® purification apparatus (silica gel, 3 to 10% ethyl acetate in hexanes)

실험 절차

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.

출처