Reaction #45816

Reaction equation

Methyl 4-acetylamino-5-bromosalicylate

benzyltrimethylammonium dichloroiodate

sodium bicarbonate

→

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

Solvents

methylene chloride

methanol

Conditions

Workup

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

Procedure

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.

Source