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

HRID 29232ノート

反応式

HRID 29232 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 129669614-Bromo-2-hydroxybenzonitrile収率 95.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a47f92932a3a4b5ba0fbbe4289868a2f
出典データセット
uspto-grants-2008_09
特許番号
US07420066B2

反応ノート

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