Réaction #77565

Équation de réaction

4-iodo-2,6-dimethoxybenzoic acid

dimethylformamide

oxalyl chloride

triethylamine

→

title compound

Rendement 97.3%

4-Ethoxycarbonyl-1-iodo-3,5-dimethoxybenzene

Rendement 97.3%

Solvants

methylene chloride

ethanol

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 30 minutes
2. 2
   Concentrationconcentrated under reduced pressure
3. 3
   LavageA solution of the residue in diethyl ether was washed successively with water, 0.1 M hydrochloric acid and brine
4. 4
   Séchagedried over anhydrous sodium sulfate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   AutreThe residue was purified by column chromatography on silica gel

Mode opératoire

To a solution of 4-iodo-2,6-dimethoxybenzoic acid (603.0 mg, 1.96 mmol), synthesized by the process described in Reference Example 11, in methylene chloride (12 mL) were added dimethylformamide (0.020 mL, 0.26 mmol) and oxalyl chloride (0.26 mL, 3.0 mmol). After stirring at room temperature for 30 minutes, the resulting solution was poured into an ice-cold solution of triethylamine (0.50 mL, 3.6 mmol) in ethanol (10 mL). The reaction mixture was stirred at room temperature for 30 minutes and concentrated under reduced pressure. A solution of the residue in diethyl ether was washed successively with water, 0.1 M hydrochloric acid and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield the title compound as a colorless oil (641.0 mg, yield: 97%).

Source