Reaction #84034

Reaction equation

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

triethylamine

diethyl phosphite

→

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

Yield 97.0%

Solvents

tetrahydrofurane

Conditions

Workup

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

Procedure

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