反応 #45816

反応方程式

Methyl 4-acetylamino-5-bromosalicylate

benzyltrimethylammonium dichloroiodate

sodium bicarbonate

→

Methyl 4-acetylamino-5-bromo-3-iodosalicylate

溶媒

methylene chloride

methanol

反応条件

後処理

1. 1
   その他The reaction liquid
2. 2
   ろ過was filtered
3. 3
   濃縮the filtrate was concentrated under reduced pressure
4. 4
   workup.ADDITIONsaturated ammonium chloride water was added to the residue
5. 5
   抽出followed by extraction twice with chloroform
6. 6
   洗浄the organic layer was washed with saturated sodium thiosulfate water
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   ろ過After filtration and concentration under reduced pressure
9. 9
   その他the eluate with chloroform/methanol (50:1) gave the entitled compound (889 mg, quant.) as a pale yellow solid

実験手順

Methyl 4-acetylamino-5-bromosalicylate (I-249) (576 mg, 2.0 mmol) was dissolved in a mixed liquid of methylene chloride (20 ml) and methanol (10 ml), then benzyltrimethylammonium dichloroiodate (835 mg, 2.4 mmol) and sodium bicarbonate (1.1 g, 13.0 mmol) were added, followed by stirring at room temperature for 30 hours. The reaction liquid was filtered, the filtrate was concentrated under reduced pressure, then saturated ammonium chloride water was added to the residue, followed by extraction twice with chloroform, then the organic layer was washed with saturated sodium thiosulfate water, and dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with chloroform/methanol (50:1) gave the entitled compound (889 mg, quant.) as a pale yellow solid.

出典