Water → 1-nitro-4-[(phenylsulfanyl)methyl]benzene

HRID 856669Notes

Reaction equation

HRID 856669 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1)([O-:17])=[O:16].O>C1COCC1>[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22][S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 7369211-nitro-4-[(phenylsulfanyl)methyl]benzeneYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzenethiol (13.2 g) was dissolved in THF (100 ml), and to this solution was added triethylamine (17.1 ml) and then 4-nitrobenzyl bromide (21.6 g). The reaction solution was stirred for 30 minutes at room temperature, 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 (=10/1), to give 1-nitro-4-[(phenylsulfanyl)methyl]benzene (20.7 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. washthe obtained residue was washed with hexane/ethyl acetate (=10/1)

Sources & evidence

ORD record
ord-afeb06a5705d4c21a7f8ce27bc089c54
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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