Citric Acid → 2-Fluorothioanisole

HRID 1241740Notes

Reaction equation

HRID 1241740 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].IC.[C:11](=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH3:11]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 5202162-Fluorothiophenol

Product 1

HCID 27747622-FluorothioanisoleYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A deoxygenated solution of 2-fluorothiophenol (10 g, 78 mmol) in anhydrous DMF (10 mL) was treated with iodomethane (4.9 mL, 78 mmol) and potassium carbonate (10.8 g, 78 mmol). The reaction mixture was stirred at room temperature for 1 hour. A thin layer chromotography (100% hexanes) sample indicated that the reaction had not gone to completion, so an additional equivalent of base and iodomethane were added and the reaction mixture was stirred overnight at room temperature. The reaction was acidified with 10% aqueous citric acid and extracted with hexanes (2×125 mnL). The combined organic extracts were washed with brine, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure to provide the desired compound as a pale yellow oil (yield: 6.68 g; 60%).

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. extractionextracted with hexanes (2×125 mnL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-af2cc73e897149049dd2673d4b0d7d4c
Source dataset
uspto-grants-2006_10
Patent number
US07115591B2

Reaction notes

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