2-Bromoethanol → Ethanol, 2-[(4-nitrophenyl)thio]-

HRID 856707Notes

Reaction equation

HRID 856707 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].Br[CH2:14][CH2:15][OH:16]>CO>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:14][CH2:15][OH:16])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 14798Sodium HydroxideHCID 158094-Nitrobenzenethiol

Product 1

HCID 83307Ethanol, 2-[(4-nitrophenyl)thio]-Yield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-nitrobenzenethiol (10 g) was dissolved in methanol (100 ml), 3N sodium hydroxide (32.2 ml) was added to the mixture, and 2-bromoethanol (9.7 g) was added dropwise to the mixture. The mixture was stirred for 1 hour at room temperature, the solvent was removed under reduced pressure, and water was added to the obtained residue, and the mixture was 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 2-[(4-nitrophenyl)sulfanyl]ethanol (10.6 g).

Workup

  1. additionwas added dropwise to the mixture
  2. customthe solvent was removed under reduced pressure, and water
  3. additionwas added to the obtained residue
  4. extractionthe mixture was extracted 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-aba4679424474fc4bd449cea98b60f54
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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