Aluminum(III) Chloride → 4-Bromo-2-hydroxybenzonitrile

HRID 29232

반응식

HRID 29232 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10]C)[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([OH:10])[CH:3]=1

참가 물질

5

반응물 2

HCID 6451240Aluminum(III) ChlorideHCID 223467024-Bromo-2-methoxybenzonitrile

생성물 1

HCID 129669614-Bromo-2-hydroxybenzonitrile수율 95.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

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).

후처리

  1. waitthe mixture left
  2. temperatureto reflux under argon overnight
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed at reduced pressure

출처 및 근거

ORD 기록
ord-a47f92932a3a4b5ba0fbbe4289868a2f
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420066B2

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