Reacción #1936680

Ecuación de reacción

adamantan-1-ylmethanol

sodium hydride

4-fluoro-3-bromobenzonitrile

→

title compound

Rendimiento 80.9%

4-(adamantan-1-ylmethoxy)-3-bromobenzonitrile

Rendimiento 80.9%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued at ambient temperature for 17 h
3. 3
   Temperaturacooled to 0° C.
4. 4
   Otroquenched with saturated ammonium chloride solution (20 mL)
5. 5
   OtroThe volatiles were removed by evaporation in vacuo
6. 6
   LavadoThe residue was washed with water and diethyl ether

Procedimiento

To a mixture of adamantan-1-ylmethanol (12.47 g, 75.00 mmol) in anhydrous tetrahydrofuran (100 mL) was added sodium hydride (60% w/w in mineral oil, 3.30 g, 82.50 mmol) at 0° C. The resulting mixture was stirred at ambient temperature for 2 h, followed by the addition of 4-fluoro-3-bromobenzonitrile (15.00 g, 75.00 mmol). Stirring was continued at ambient temperature for 17 h, cooled to 0° C. and quenched with saturated ammonium chloride solution (20 mL). The volatiles were removed by evaporation in vacuo. The residue was washed with water and diethyl ether to give the title compound as a pale yellow solid (21.00 g, 80%): 1H NMR (300 MHz, CDCl3) δ 7.80-7.78 (m, 1H), 7.56-7.51 (m, 1H), 6.88-6.84 (m, 1H), 3.57 (s, 3H), 2.02 (br s, 3H), 1.73-1.55 (m, 12H).

Fuente