Reacción #45447

Ecuación de reacción

4-bromo-2-iodo-phenylamine

thiacetamide

→

desired product

Rendimiento 48.2%

6-bromo-2-methyl-1,3-benzothiazole

Rendimiento 48.2%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropartitioned between water and ethyl acetate
2. 2
   SecadoThe organic phase was dried (Na2SO4)
3. 3
   Concentraciónconcentrated
4. 4
   OtroThe concentrate was purified by flash chromatography on silica gel using 20% hexanes/methylene chloride

Procedimiento

A solution of 4-bromo-2-iodo-phenylamine (1.5 g, 5.0 mmol), thiacetamide (381 mg, 5.0), cupric oxide (280 mg, 3.5 mmol), dppf (56 mg, 0.10 mmol), Pd2(dba)3 (48 mg, 0.052 mmol) in DMF was heated at 60° C. for 1 hour, cooled to room temperature, partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and concentrated. The concentrate was purified by flash chromatography on silica gel using 20% hexanes/methylene chloride to give 550 mg (40% yield) of the desired product. MS (ESI(+)) m/e 227.8, 229.8 (M+H)+.

Fuente