Reacción #822011

Ecuación de reacción

NaI

N,N′-dimethylethylenediamine

methyl 5-bromobenzo[b]thiophen-2-carboxylate

→

methyl 5-iodobenzo[b]thiophen-2-carboxylate

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadoafter rinsing again with argon the reaction mixture
2. 2
   Temperaturawas heated overnight to 110° C
3. 3
   TemperaturaAfter cooling
4. 4
   Extracciónexhaustively extracted with EtOAc
5. 5
   Lavadothe combined organic phases were twice washed with water
6. 6
   Secadodried over magnesium sulfate
7. 7
   Otrothe residue was triturated with DIPE and MTBE, suction
8. 8
   Filtraciónfiltered
9. 9
   Otrodried in the air
10. 10
    Otro6.4 minutes (method B)

Procedimiento

Under an argon atmosphere 0.35 g (1.84 mmol) of CuI, 5.53 g (36.88 mmol) of NaI, and 0.39 mL (3.67 mmol) of N,N′-dimethylethylenediamine were added to a solution of 5.0 g (18.4 mmol) of methyl 5-bromobenzo[b]thiophen-2-carboxylate in 18 mL of 1,4-dioxane and after rinsing again with argon the reaction mixture was heated overnight to 110° C. After cooling, the reaction mixture was combined with 30% aqueous ammonia and water, exhaustively extracted with EtOAc, and the combined organic phases were twice washed with water and dried over magnesium sulfate. After the desiccant and solvent had been eliminated, the residue was triturated with DIPE and MTBE, suction filtered, and dried in the air. Yield: 3.4 g (58% of theoretical); C10H7IO2S (M=318.132); calc.: molpeak (M)+: 318; found: molpeak (M)+: 318; HPLC-MS: 6.4 minutes (method B).

Fuente