Dimethyl Disulfide → 5-(2-Bromo-4-nitrophenoxy)-2-(methylthio)phenol

HRID 325823ノート

反応式

HRID 325823 の反応式
[Br:1][C:2]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.[CH3:19][S:20]Cl.CSSC.ClCl>C(Cl)Cl>[Br:1][C:2]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([S:20][CH3:19])=[C:7]([OH:11])[CH:6]=1

参加物

6

反応物 4

HCID 12232Dimethyl DisulfideHCID 24526ChlorineHCID 138595MethanesulfenylchlorideHCID 204628063-(2-Bromo-4-nitrophenoxy)phenol

生成物 1

HCID 204628205-(2-Bromo-4-nitrophenoxy)-2-(methylthio)phenol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-20 °C

実験手順

3-(2-Bromo-4-nitrophenoxy)phenol (0.01 mole) and methylene chloride (200 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer and addition funnel. The mixture is stirred until dissolved and cooled to about -20° C. A solution of methyl sulfenyl chloride freshly prepared by reacting dimethyl disulfide (0.015 mole) with chlorine (0.18 mole) in methylene chloride (100 ml) is then added dropwise to the reaction vessel over a period of about 40 minutes. After the addition is completed stirring is continued for 30 minutes with cooling and 30 minutes at room temperature. After this time the reaction mixture is washed with water (200 ml) with 5% aqueous sodium bicarbonate (200 ml) and again with water (200 ml). The washed solution is then dried by passing it through a phase separator. The dried solution is stripped of solvent under reduced pressure and the residue chromatographed using a clay column and hexane/ethyl acetate as the eluant. The fractions containing the product are combined and stripped of solvent to yield the desired product 5-(2-bromo-4-nitrophenoxy)-2-(methylthio)phenol as the residue.

後処理

  1. customequipped with a mechanical stirrer and addition funnel
  2. dissolutionuntil dissolved
  3. additionis then added dropwise to the reaction vessel over a period of about 40 minutes
  4. additionAfter the addition
  5. stirringis completed stirring
  6. temperaturewith cooling and 30 minutes at room temperature
  7. washAfter this time the reaction mixture is washed with water (200 ml) with 5% aqueous sodium bicarbonate (200 ml) and again with water (200 ml)
  8. customThe washed solution is then dried
  9. customthe residue chromatographed
  10. additionThe fractions containing the product

出典と根拠

ORDレコード
ord-d35bc6de057b45b9a54294f736728743
出典データセット
uspto-grants-1984_04
特許番号
US04443248

反応ノート

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