Hydrochloric Acid → HCID 11356278, compound

HRID 1837948Notes

Reaction equation

HRID 1837948 reaction equation
I[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[OH-].[K+].[F:9][C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1.Cl>CN(C=O)C>[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:2]2[S:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 189212-IodothiopheneHCID 677894-Fluorothiophenol

Product 1

HCID 11356278HCID 11356278, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

To a degassed mixture of 2-iodothiophene (0.87 mL, 7.88 mmol), Cu2O (0.56 g, 3.9 mmol) and KOH (0.44 g, 7.8 mmol) in DMF (7.8 mL) was slowly added 4-fluorobenzenethiol (0.33 mL, 7.8 mmol). The resulting mixture was heated at 135° C. for 15 h, allowed to cool to room temperature and poured into a 0° C. 6N HCl solution. After 15 min. the precipitate was filtered and washed with benzene. The filtrate was extracted with benzene, dried (MgSO4) and concentrated under reduced pressure to give 2-(4-fluorophenylthio)thiophene (1.13 g, 69%) as a pale yellow oil: TLC (10% EtOAc/hex) Rf 0.49; HPLC ES-MS m/z (rel intensity) 210 (M+, 100).

Workup

  1. temperatureto cool to room temperature
  2. additionpoured into a 0° C
  3. filtrationAfter 15 min. the precipitate was filtered
  4. washwashed with benzene
  5. extractionThe filtrate was extracted with benzene
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aeb1776143cd4d2aaac62e730262a303
Source dataset
uspto-grants-2004_08
Patent number
US06784167B2

Reaction notes

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