p-Chlorothiophenol → HCID 43413016, compound

HRID 716718Notes

Reaction equation

HRID 716718 reaction equation
[O-]CC.[Na+].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=1)=[O:16]>C(O)C>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([S:23][CH3:24])=[CH:19][CH:18]=2)=[O:16])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 2723922Sodium ethoxideHCID 27375232-Bromo-1-(4-methylsulfanylphenyl)ethanone

Product 1

HCID 43413016HCID 43413016, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring mixture of sodium ethoxide (13.32 g, 196 mmol) in ethanol (IL) in a 2 L RBF was added 4-chlorothiophenol (26.0 g, 179 mmol), followed by 2-bromo-1-[4-(methylsulfanyl)phenyl]ethanone (40 g, 163 mmol). The reaction mixture was heated to reflux until all solid dissolved, hot filtered through a fritted funnel, then allowed to cool slowly to room temperature, then to 0° C. in an ice bath. The title compound was isolated as pink needle-like crystals (43.9 g, 87%) by filtration. LCMS M+1=309.2.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux until all solid
  3. dissolutiondissolved
  4. filtrationhot filtered through a fritted funnel
  5. customto 0° C.

Sources & evidence

ORD record
ord-674abdfad84d486b810fbbf156a2e00e
Source dataset
uspto-grants-2015_11
Patent number
US09193697B2

Reaction notes

Loading…