Diethyl Carbonate → 3-Fluorothioanisole

HRID 51019

Reaction equation

HRID 51019 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](=O)(OCC)OCC.C([O-])([O-])=O.[K+].[K+]>C1OCCOCCOCCOCCOCCOC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8][CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 11430Potassium CarbonateHCID 75710m-Fluorobenzenethiol

Product 1

HCID 27591643-FluorothioanisoleYield 97%

Reagents, catalysts & solvents 1

HCID 2855718-Crown-6Catalyst

Conditions

Temperature
100 °C

Procedure

To a solution of 3-fluorothiophenol (4.73 g, 37.0 mmol) in diethyl carbonate (11 mL, 129 mmol) was added K2CO3 (7.67 g, 55.5 mmol) and 18-crown-6 ether (100 mg, 0.37 mmol). The reaction mixture was refluxed at 100° C. for 12 h. The reaction mixture was cooled to 20° C. then quenched by addition of H2O and extracted with Et2O. The combine organic solution was washed with H2O and brine, dried over MgSO4.to give 1-fluoro-3-(methylsulfanyl)benzene (5.10 g, 97%) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled to 20° C.
  2. customthen quenched by addition of H2O
  3. extractionextracted with Et2O
  4. washThe combine organic solution was washed with H2O and brine
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-0d6e430934f24b54a20264e763a83e3e
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Linked notes

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