Reacción #84034

Ecuación de reacción

2,2-dibromo-1-(6-bromonaphthalen-2-yl)ethanone

triethylamine

diethyl phosphite

→

2-bromo-1-(6-bromonaphthalen-2-yl)ethanone

Rendimiento 97.0%

Disolventes

tetrahydrofurane

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe reaction mixture was filtrated
2. 2
   Otrothe solvent was removed in vacuum
3. 3
   workup.DISSOLUTIONThe obtained residue was dissolved in ethyl acetate (1.2 L)
4. 4
   Lavadowashed with water
5. 5
   OtroThe organic layer was separated
6. 6
   Secadodried over sodium sulphate
7. 7
   Filtraciónfiltrated
8. 8
   Concentraciónconcentrated

Procedimiento

2,2-dibromo-1-(6-bromonaphthalen-2-yl)ethanone (90.0 g, 221 mmol, 1.00) was dissolved in tetrahydrofurane (800 mL), triethylamine (27.67 mL, 199 mmol, 0.9 equiv.) was added followed by diethyl phosphite (45.8 g, 332 mmol, 1.50 equiv.). The reaction mixture was stirred overnight. The reaction mixture was filtrated and the solvent was removed in vacuum. The obtained residue was dissolved in ethyl acetate (1.2 L) and washed with water. The organic layer was separated, dried over sodium sulphate, filtrated and concentrated to yield crude 2-bromo-1-(6-bromonaphthalen-2-yl)ethanone (70.3 g). Recrystallization from acetonitrile gave 30 g (first batch) and 6.5 g (second batch) of 2-bromo-1-(6-bromonaphthalen-2-yl)ethanone (50%)

Fuente