Methyl iodide → 4-Bromo-2-fluorothioanisole

HRID 2103627Notes

Reaction equation

HRID 2103627 reaction equation
O.O.O.[F-].[CH2:5]([N+](CCCC)(CCCC)CCCC)CCC.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([S:29][Si](C(C)C)(C(C)C)C(C)C)=[C:25]([F:40])[CH:24]=1.C(=O)([O-])[O-].[K+].[K+].CI>C1COCC1>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([S:29][CH3:5])=[C:25]([F:40])[CH:24]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 67084425HCID 67084425, compound

Product 1

HCID 219340644-Bromo-2-fluorothioanisoleYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add tetrabutylammonium fluoride trihydrate (546 mg, 1.73 mmol) to a mixture of (4-bromo-2-fluoro-phenylsulfanyl)-triisopropyl-silane (570 mg, 1.57 mmol) and potassium carbonate (650 mg, 4.71 mmol) in 20 mL THF and stir at r.t. for 1 h. Add methyl iodide, stir for 1 h and concentrate to remove THF. Add 20 mL water, extract with diethylether, dry the combined organic extracts over sodium sulfate, filtrate and concentrate under reduced pressure to obtain 4-bromo-2-fluoro-1-methylsulfanyl-benzene (347 mg) as a colorless liquid, which was used for following conversions without further purifications. MS (m/e): 220 [(79Br)M], 222 [(81Br)M].

Workup

  1. concentrationconcentrate
  2. customto remove THF
  3. additionAdd 20 mL water
  4. extractionextract with diethylether
  5. dry with materialdry the combined organic extracts over sodium sulfate, filtrate
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-577bd3b1aeaf4ff7a9f953b1bb71abaf
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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