Benzyl Bromide → 4-(benzylsulfanyl)aniline

HRID 856675Notes

Reaction equation

HRID 856675 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CO>[CH2:11]([S:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 145104-AminothiophenolHCID 14798Sodium Hydroxide

Product 1

HCID 50841454-(benzylsulfanyl)aniline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-aminothiophenol (6.0 g) was dissolved in methanol (120 ml), aqueous solution of sodium hydroxide (2.7 g, 36 ml) was added to the mixture, benzyl bromide (6.8 ml) was added to the mixture at 0° C., and the mixture was stirred for 2 hours at room temperature. The solvent was removed under reduced pressure, and the obtained residue was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure and the obtained residue was washed with hexane/ethyl acetate, to give 4-(benzylsulfanyl)aniline (7.0 g).

Workup

  1. additionwas added to the mixture at 0° C.
  2. customThe solvent was removed under reduced pressure
  3. additionthe obtained residue was added to water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. washthe obtained residue was washed with hexane/ethyl acetate

Sources & evidence

ORD record
ord-f72142bb87cc42ac8bbc93412707adbb
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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