تفاعل #57510

معادلة التفاعل

4-bromo-2-methoxy-benzonitrile

aluminum chloride

→

4-bromo-2-hydroxy-benzonitrile

المردود 95.2%

المذيبات

ethyl acetate

methylene chloride

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   workup.WAITthe mixture left
2. 2
   درجة الحرارةto reflux under argon overnight
3. 3
   غسيلwashed with water, brine
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   أخرىThe solvent was removed at reduced pressure

الإجراء التجريبي

To a stirred solution of 4-bromo-2-methoxy-benzonitrile (4.60 g, 21.7 mmol) in methylene chloride (20 mL) was added aluminum chloride (14.5 g, 108 mmol). After stirring under an argon atmosphere for 10 min, more methylene chloride (30 mL) was added, and the mixture left to reflux under argon overnight. The reaction was then diluted with ethyl acetate, washed with water, brine, and dried over magnesium sulfate. The solvent was removed at reduced pressure, providing (4.09 g, 95.2%) of 4-bromo-2-hydroxy-benzonitrile as a slightly gray-colored product. 1H-NMR (CDCl3) δ 7.35 (d, J=8.4 Hz, 1H), 7.19 (d, J=1.4 Hz, 1H), 7.14 (dd, J=8.4, 1.4 Hz, 1H), 6.15 (s, 1H); TLC Rf=0.78 (50% ethyl acetate—hexane).

المصدر