Iodoethane → 3,5-Dichlorophenyl ethyl sulfide

HRID 75230

Reaction equation

HRID 75230 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.I[CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>O>[CH2:11]([S:9][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=1)[CH3:12]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27360963,5-Dichlorobenzenethiol

Product 1

HCID 597520583,5-Dichlorophenyl ethyl sulfideYield 97.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3,5-dichlorobenzenethiol (1.50 g, 8.4 mmol), iodoethane (1.34 mL, 16.8 mmol), potassium carbonate (1.74 g, 12.6 mmol) and methylene chloride (10 mL) was stirred at 25° C. for 30 minutes. The reaction was diluted with water and extracted with ethyl acetate three times, dried over sodium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel to give the desired product (1.69 g, 97%). LC/MS: 207 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9402da52b7b946efb3caf5900f1f5e5b
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Linked notes

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