Reaction #217839

Reaction equation

3-methoxyphenol

I2

→

2-iodo-5-methoxyphenol

Yield 33.8%

Solvents

CHCl3

CHCl3

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction was stirred at room temperature for 16 hours
2. 2
   OtherSolids were removed by filtration
3. 3
   WashThe filtrate was washed with 5% Na2S2O3(500 mL), saturated NaHCO3, brine
4. 4
   Dryingdried over MgSO4
5. 5
   Concentrationconcentrated
6. 6
   OtherThe crude mixture was triturated with carbon tetrachloride

Procedure

I2 (40.9 g, 161.1 mmol) was dissolved in CHCl3 (850 mL) with stirring over 1 hour. The solution was added slowly into a reaction mixture of 3-methoxyphenol 5-A (20 g, 161.1 mmol) and silver trifluoroacetate in 200 mL CHCl3 over 1.5 hours. The reaction was stirred at room temperature for 16 hours. Solids were removed by filtration. The filtrate was washed with 5% Na2S2O3(500 mL), saturated NaHCO3, brine, dried over MgSO4 and concentrated. The crude mixture was triturated with carbon tetrachloride to give 2-iodo-5-methoxyphenol 5-B (13.6 g) as a white solid. The remaining crude products were purified by silica gel column chromatography eluted with CH2Cl2to give 28.2 g of compound 5-B.

Source