反応 #74463

反応方程式

5-bromo-2-chlorobenzyl alcohol

5-Bromo-2-chlorobenzyl alcohol

triisopropylsilyl chloride

→

title compound

収率 95.0%

(5-Bromo-2-chlorobenzyloxy)triisopropylsilane

収率 95.0%

溶媒

N,N-dimethylformamide

ammonium chloride

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate
2. 2
   洗浄The organic layer was washed with water
3. 3
   乾燥brine, dried over magnesium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuo
6. 6
   その他The crude residue was purified on Biotage® purification apparatus (silica gel, 3 to 10% ethyl acetate in hexanes)

実験手順

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.

出典