Potassium Carbonate → HCID 9989971, compound

HRID 849546Notes

Reaction equation

HRID 849546 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Cl[CH2:10][CH2:11][CH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:10][CH2:11][CH2:12][OH:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 677894-Fluorothiophenol

Product 1

HCID 9989971HCID 9989971, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Part A: A solution of 10 g (78 mmol) of 4-fluorothiophenol and 8 g (86 mM) of 3-chloro-1-propanol in 80 mL of anhydrous DMF was purged with nitrogen for 20 min., then treated with 32 g (234 mM) of potassium carbonate. After one hour, the reaction mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with brine (3×), dried (MgSO4), and concentrated to afford 16 g of crude product. The crude product was chromatographed on silica gel using 30-45% ethyl acetate/hexane to yield 12 g of pure 3-[(4-fluorophenyl)thio]propan-1-ol, m/z=203 (M+NH4).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic layer was washed with brine (3×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto afford 16 g of crude product
  8. customThe crude product was chromatographed on silica gel using 30-45% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c2c60dff62594ab9a699fd9791752e65
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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