4-Fluorothiophenol → {2-[(4-Fluorophenyl)sulfanyl]ethyl}(methyl)amine

HRID 915650Notes

Reaction equation

HRID 915650 reaction equation
Br.Br[CH2:3][CH2:4][NH:5][CH3:6].[F:7][C:8]1[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=1.CC(C)([O-])C.[K+]>C(#N)C>[F:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][CH2:3][CH2:4][NH:5][CH3:6])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 677894-FluorothiophenolHCID 12735740(2-Bromoethyl)(methyl)amine hydrobromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 60686925{2-[(4-Fluorophenyl)sulfanyl]ethyl}(methyl)amineYield 61.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Reflux a mixture of (2-bromoethyl)methylamine hydrobromic acid salt (500 mg, 2.28 mmol), 4-fluorobenzenethiol (0.243 mL, 2.28 mmol), and potassium t-butoxide (512 mg, 4.56 mmol) in acetonitrile (10 mL) for 17 hours. Remove the solvent under vacuum and dissolve the residue in ether and 5 N sodium hydroxide solution. Extract the organic layer with 1 N hydrochloric acid solution. Neutralize the acidic aqueous layer with 5 N sodium hydroxide solution and extract twice with ether. Dry the combined ether extracts over magnesium sulfate and reduce under vacuum to give 260 mg of the titled compound as an oil.

Workup

  1. temperatureReflux
  2. customRemove the solvent under vacuum
  3. dissolutiondissolve the residue in ether
  4. extractionExtract the organic layer with 1 N hydrochloric acid solution
  5. extractionNeutralize the acidic aqueous layer with 5 N sodium hydroxide solution and extract twice with ether
  6. dry with materialDry the combined ether

Sources & evidence

ORD record
ord-e78f6af1cfc2420dbc8ed908845c3916
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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