Reaction #816411

Reaction equation

3-Formylamino-thiophene

N-iodosuccinimide

→

product

Yield 90.5%

2-Iodo-3-formylaminothiophene

Yield 90.5%

Solvents

tetrachlormethane

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   workup.DISSOLUTIONThe solids were dissolved in ethyl acetate
3. 3
   Washwashed three times with sodium hydroxide (10% solution)
4. 4
   Washwashed with brine
5. 5
   Dryingdried over sodium sulfate
6. 6
   OtherEvaporation of the solvents and chromatography of the residue over silica gel (hexane:ethyl acetate 2:1)

Procedure

3-Formylamino-thiophene (21 g), N-iodosuccinimide (37.2 g) and tetrachlormethane (200 ml) were refluxed together for 3 hours. The reaction mixture was cooled to 0-5° C. and filtered. The solids were dissolved in ethyl acetate, washed three times with sodium hydroxide (10% solution), washed with brine and dried over sodium sulfate. Evaporation of the solvents and chromatography of the residue over silica gel (hexane:ethyl acetate 2:1) yielded 37.8 g of product (m.p. 100-107° C.) which was directly used in Step B.

Source