Reacción #1257057

Ecuación de reacción

Bromomethyl-2-chloro-5-iodo-benzene

Bromomethyl-2-chloro-5-iodobenzene

potassium phthalimide

→

63

Rendimiento 95.4%

N-(2-Chloro-5-iodobenzyl)phthalimide

Rendimiento 95.4%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling
2. 2
   Filtraciónthe suspension was filtered
3. 3
   Concentraciónconcentrated in vacuo
4. 4
   Otrothe residue was partitioned between water (30 mL) and Et2O (30 mL)
5. 5
   ExtracciónThe aqueous phase was extracted with ether (20 mL×3)
6. 6
   SecadoThe combined organic phases were dried over Na2SO4
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated

Procedimiento

Bromomethyl-2-chloro-5-iodo-benzene (60) (400 mg, 1.2 mmol) and potassium phthalimide (693 mg, 1.5 mmol) were stirred in dry DMF (20 mL) and heated to 80° C. for 3 hours. After cooling, the suspension was filtered and concentrated in vacuo, and the residue was partitioned between water (30 mL) and Et2O (30 mL). The aqueous phase was extracted with ether (20 mL×3). The combined organic phases were dried over Na2SO4, filtered and concentrated to give 63 (455 mg, 95%). 1H NMR (CDCl3, 300 MHz) δ 7.92-7.86 (m, 2H), 7.78-7.75 (m, 2H), 7.54-7:50 (m, 2H), 7.10 (d, J=8.4 Hz, 1H), 4.93 (s, 2H). MS (m/e) (API-ES) 397.9 (M)+, m.p. 134-136° C.

Fuente