Reaction #2460298

Reaction equation

thiosalicylic acid

3-iodoanisole

potassium carbonate

→

2-(3-methoxyphenylthio)benzoic acid

Solvents

N-methylpyrrolidinone

Conditions

Workup

1. 1
   Otherby sparging with nitrogen for 10 min
2. 2
   Temperaturecooled
3. 3
   workup.ADDITIONThe reaction mixture was poured onto a mixture of 500 g of ice plus 40 mL of concentrated HCl
4. 4
   OtherThe resulting precipitate was collected
5. 5
   Washwashed with water
6. 6
   Otherdried
7. 7
   workup.DISSOLUTIONThe precipitate was dissolved in acetone
8. 8
   Filtrationfiltered through Celite
9. 9
   Concentrationconcentrated
10. 10
    OtherThe product was purified by recrystallization from aqueous ethanol
11. 11
    OtherA tan powder was obtained

Procedure

First, 2-(3-methoxyphenylthio)benzoic acid was prepared. A stirred mixture of thiosalicylic acid (3.57 g, 23 mmol), 3-iodoanisole (5.42 g, 23 mmol), potassium carbonate (7.04 g, 51 mmol), copper powder (0.29 g, 5 mmol), and N-methylpyrrolidinone (75 mL) was deaerated by sparging with nitrogen for 10 min, heated at 165° C. for 2 h, and then cooled to ambient. The reaction mixture was poured onto a mixture of 500 g of ice plus 40 mL of concentrated HCl. The resulting precipitate was collected, washed with water, and dried. The precipitate was dissolved in acetone and filtered through Celite, then concentrated to deposit a crude product. The product was purified by recrystallization from aqueous ethanol. A tan powder was obtained, mass: 4.60 g (76% of theory).

Source