تفاعل #66476

معادلة التفاعل

1-methylsulfanyl-4-nitro-benzene

sodium thiosulphate

periodic acid

→

(RS)-1-(methylsulfinyl)-4-nitrobenzene

المذيبات

acetonitrile

—

ice water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAt the start of heat evolution, the mixture is transiently cooled with an ice-bath, so that the temperature
2. 2
   أخرىdoes not rise above 30° C
3. 3
   workup.STIRRINGthe mixture is stirred at room temperature for a further 10 mins
4. 4
   استخلاصextracted with DCM
5. 5
   غسيلThe combined organic phases are washed with saturated NaCl solution
6. 6
   تجفيفdried (Na2SO4)
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated
9. 9
   أخرىThe remaining residue is recrystallised from toluene
10. 10
    أخرى23.6 g (128.0 mmol, corresponding to 86% of theor.) of the product is obtained

الإجراء التجريبي

A suspension of 25.0 g (147.8 mmol) 1-methylsulfanyl-4-nitro-benzene and 0.69 g (4.2 mmol) iron(III) chloride (anhydrous) in 120 ml acetonitrile is treated with 36.0 g (158.1 mmol) periodic acid and stirred at room temperature. At the start of heat evolution, the mixture is transiently cooled with an ice-bath, so that the temperature does not rise above 30° C. After the heat evolution has subsided, the mixture is stirred at room temperature for a further 10 mins. The mixture is poured into a solution of 150 g sodium thiosulphate in 1000 ml ice-water and then extracted with DCM. The combined organic phases are washed with saturated NaCl solution, dried (Na2SO4), filtered and concentrated. The remaining residue is recrystallised from toluene. 23.6 g (128.0 mmol, corresponding to 86% of theor.) of the product is obtained.

المصدر