Reacción #5389

Ecuación de reacción

1-naphthol

2-bromo-1-naphthol

N-bromo-t-butylamine

bromonaphthol

potassium carbonate

→

2-bromo-1-methoxynaphthalene

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITOver a 2-hous period
2. 2
   workup.ADDITION95 mL of dimethylsulate was added dropwise to the mechanically stirred reaction mixture
3. 3
   FiltraciónThe solids were filtered
4. 4
   Otroto yield a dark brown oil
5. 5
   OtroInitial purification
6. 6
   workup.DISTILLATIONwas accomplished by vacuum distillation (80°-120° C., 0.2 Torr)
7. 7
   Otrofollowed by further purification by HPLC with hexane

Procedimiento

1-naphthol was converted into 2-bromo-1-naphthol by reaction with a slurry of N-bromo-t-butylamine at -78° C. according to the procedure described in Pearson, Wysong, Breder, J. Org. Chem. 32, 2358 (1967). To a solution of 1 mole (crude) of the bromonaphthol in 750 mL of acetone was added 175 g of potassium carbonate. Over a 2-hous period, 95 mL of dimethylsulate was added dropwise to the mechanically stirred reaction mixture. The resulting slurry was stirred at 25° C. overnight. The solids were filtered and the solution was stripped to yield a dark brown oil. Initial purification was accomplished by vacuum distillation (80°-120° C., 0.2 Torr) followed by further purification by HPLC with hexane to yield 145 g of 2-bromo-1-methoxynaphthalene as a pale yellow oil. NMR confirmed the structure.

Fuente