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Water → 2-Chloro-4-mercaptophenol

HRID 2209655
ノート
印刷プレビュー

反応式

HRID 2209655 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([SH:10])[CH:5]=[CH:6][C:7]=1[O:8]C.B(Br)(Br)Br.O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([SH:10])[CH:5]=[CH:6][C:7]=1[OH:8]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 25134Boron tribromideHCID 132380123-Chloro-4-methoxybenzene-1-thiol

生成物 1

HCID 143697432-Chloro-4-mercaptophenol収率 97.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

324 mg of said di(3-chloro-4-methoxyphenyl)disulfide was dissolved in 10 ml of ethanol, followed by addition of 106 mg of sodium borohydride. The mixture was stirred over 2 hours at room temperature. The solution thus reacted was made weakly acidic by addition of dilute hydrochloric acid. The product was extracted twice with ethyl acetate. The organic layer was washed with saturated salt water and then dried over sodium sulfate anhydride. The solvent was distilled out under reduced pressure. The resulting crude product was purified by flash column chromatography (hexane: ethyl acetate =15:1), whereby 239 mg of 3-chloro-4-methoxybenzenethiol was obtained. 231 mg of the resulting 3-chloro-4-methoxybenzenethiol was dissolved in 4 ml dichloromethane, followed by cooling to 0° C. 4 ml of boron tribromide in dichloromethane was added dropwise under stirring. The mixture was stirred for 2 hours under cooling on ice and then for 20 hours at room temperature. Subsequently, under cooling on ice, water was added to the solution thus reacted, and the product was extracted twice with chloroform. The organic layer was washed with saturated salt water and dried over sodium sulfate anhydride. The solvent was distilled out, whereby 208 mg of crude 3-chloro-4-hydroxybenzenethiol was obtained.

後処理

  1. stirringThe mixture was stirred for 2 hours
  2. temperatureunder cooling on ice
  3. additionwas added to the solution
  4. customthus reacted
  5. extractionthe product was extracted twice with chloroform
  6. washThe organic layer was washed with saturated salt water
  7. dry with materialdried over sodium sulfate anhydride
  8. distillationThe solvent was distilled out

出典と根拠

ORDレコード
ord-48a33ca95c9e4700a60f314a11f2e6f3
出典データセット
uspto-grants-1995_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05455267

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート