Réaction #84034

Équation de réaction

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

triethylamine

diethyl phosphite

→

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

Rendement 97.0%

Solvants

tetrahydrofurane

Conditions de réaction

Traitement

1. 1
   FiltrationThe reaction mixture was filtrated
2. 2
   Autrethe solvent was removed in vacuum
3. 3
   workup.DISSOLUTIONThe obtained residue was dissolved in ethyl acetate (1.2 L)
4. 4
   Lavagewashed with water
5. 5
   AutreThe organic layer was separated
6. 6
   Séchagedried over sodium sulphate
7. 7
   Filtrationfiltrated
8. 8
   Concentrationconcentrated

Mode opératoire

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%)

Source