反应详情

温度

85 °C

To a solution of 61.8 g of 2-hydroxy-5-methoxybenzoic acid, methyl ester in 700 ml DMF was added 14.96 g of a 60% suspension of sodium hydride in mineral oil. This was followed by addition of 50.88 g of sodium iodide, 64.64 g of copper(I)iodide, and 2.16 g of finely powdered copper metal. The mixture was heated to 85° C., for 15 minutes, then 71.7 g of 2,4-dichloronitrobenzene was added, and the reaction was stirred at 85° C. for 16 hours. The mixture was filtered, and the filtrate concentrated to an oily residue. Sodium thiosulfate, 400 ml of a 20% solution was added, followed by extraction with ethyl acetate (3×400 ml). The combined ethyl acetate extracts were washed with water (2×325 ml), dried over anhydrous sodium sulfate, then evaporated to afford a pale yellow solid, which was triturated with cyclohexane and filtered giving the title compound, mp 114°-116° C.

1. filtrationThe mixture was filtered
2. concentrationthe filtrate concentrated to an oily residue
3. additionSodium thiosulfate, 400 ml of a 20% solution was added
4. extractionfollowed by extraction with ethyl acetate (3×400 ml)
5. washThe combined ethyl acetate extracts were washed with water (2×325 ml)
6. dry with materialdried over anhydrous sodium sulfate
7. customevaporated
8. customto afford a pale yellow solid, which
9. customwas triturated with cyclohexane
10. filtrationfiltered