反応 #86634

反応方程式

Mesyl chloride

2,3,5-triiodobenzyl alcohol

diisopropylethylamine

lithium chloride

→

2,3,5-triiodobenzyl chloride

収率 90.0%

溶媒

dichloromethane

H2O

反応条件

後処理

1. 1
   抽出The resulting aqueous phase was extracted with dichloromethane (2×10 ml)
2. 2
   洗浄The combined organic extracts were washed with NaHCO3 aq (20 ml) and H2O (20 ml)
3. 3
   乾燥then dried (Na2SO4)
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   洗浄The pale yellow solid was also washed with cold absolute ethanol (25 mL)

実験手順

Mesyl chloride (4.24 ml, 56 mmol) was added dropwise into a suspension of 2,3,5-triiodobenzyl alcohol 1 (9.72 g, 20 mmol) in dry dichloromethane (140 ml) containing diisopropylethylamine (11 ml, 64 mmol) and lithium chloride (4.24 g, 100 mmol) at 0° C. under dry nitrogen gas flow. The reaction mixture was stirred 5 h at room temperature, then cold H2O (100 mL) was added. The resulting aqueous phase was extracted with dichloromethane (2×10 ml). The combined organic extracts were washed with NaHCO3 aq (20 ml) and H2O (20 ml) then dried (Na2SO4), filtered and concentrated. The pale yellow solid was also washed with cold absolute ethanol (25 mL). 9.05 g of 2,3,5-triiodobenzyl chloride in the form of a white clean solid was obtained in 90% yield.

出典