تفاعل #362361

معادلة التفاعل

2-adamantyl-5-iodophenol

dimethylsulfate

potassium carbonate

→

2-adamantyl-5-iodoanisole

المردود 81.3%

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux for 24 h
2. 2
   تركيزconcentrated in vacuo
3. 3
   أخرىThe crude product was partitioned between methylene chloride and water
4. 4
   تجفيفThe organic phase was dried over anhydrous magnesium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated

الإجراء التجريبي

A solution of 2-adamantyl-5-iodophenol (7.70 g, 21.7 mmol) in acetone (100 mL) was treated with dimethylsulfate (4.11 g, 32.6 mmol) and potassium carbonate (4.50 g, 32.6 mmol). The reaction mixture was stirred at reflux for 24 h, allowed to cool to room temperature, and concentrated in vacuo. The crude product was partitioned between methylene chloride and water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated to provide 6.5 g (81%) of 2-adamantyl-5-iodoanisole; 1H NMR (300 MHz, CDCl3) δ 7.22 (dd, J=2, 8 Hz, 1H, ArH), 7.10 (d, J=2 Hz, 1H, ArH), 6.89 (d, J=8 Hz, 1H, ArH), 3.79 (s, 3H, OCH3), 2.02 (s, 9H, adamantyl), and 1.73 (s, 6H, adamantyl); 13C NMR (75 MHz, CDCl3) δ 159.35, 138.43, 129.63, 128.25, 120.75, 91.20, 55.22 (OCH3), 40.35, 37.02, 36.92, and 28.97; MS (DCI) m/e 369 (MH+), 368 (M+), 367 (M--H)+, 135 (C10H15+). Anal. Calcd for C17H21OI: C, 55.45; H, 5.75. Found: C, 55.51; H, 5.81.

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