Реакция #1936680

Уравнение реакции

adamantan-1-ylmethanol

sodium hydride

4-fluoro-3-bromobenzonitrile

→

title compound

Выход 80.9%

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

Выход 80.9%

Растворители

tetrahydrofuran

Условия реакции

Обработка

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

Методика

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).

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