반응 #57510

반응 방정식

4-bromo-2-methoxy-benzonitrile

aluminum chloride

→

4-bromo-2-hydroxy-benzonitrile

수율 95.2%

용매

ethyl acetate

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   workup.WAITthe mixture left
2. 2
   온도to reflux under argon overnight
3. 3
   세척washed with water, brine
4. 4
   건조dried over magnesium sulfate
5. 5
   기타The solvent was removed at reduced pressure

실험 절차

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).

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