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

HRID 325823Notes

Reaction equation

HRID 325823 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d35bc6de057b45b9a54294f736728743
Source dataset
uspto-grants-1984_04
Patent number
US04443248

Reaction notes

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