반응 #45816

반응 방정식

Methyl 4-acetylamino-5-bromosalicylate

benzyltrimethylammonium dichloroiodate

sodium bicarbonate

→

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

용매

methylene chloride

methanol

반응 조건

후처리

1. 1
   기타The reaction liquid
2. 2
   여과was filtered
3. 3
   농축the filtrate was concentrated under reduced pressure
4. 4
   workup.ADDITIONsaturated ammonium chloride water was added to the residue
5. 5
   추출followed by extraction twice with chloroform
6. 6
   세척the organic layer was washed with saturated sodium thiosulfate water
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   여과After filtration and concentration under reduced pressure
9. 9
   기타the eluate with chloroform/methanol (50:1) gave the entitled compound (889 mg, quant.) as a pale yellow solid

실험 절차

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.

출처