Water → (4-Bromo-3-(difluoromethyl)phenyl)(ethyl)sulfane

HRID 1846032Notes

Reaction equation

HRID 1846032 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[CH:4][C:3]=1[CH:9]([F:11])[F:10].[CH2:12]([S-:14])[CH3:13].[Na+].O>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:14][CH2:12][CH3:13])=[CH:4][C:3]=1[CH:9]([F:11])[F:10]

Participants

5

Reactant 3

HCID 962WaterHCID 4459711Sodium ethanethiolateHCID 463116681-Bromo-2-(difluoromethyl)-4-fluorobenzene

Product 1

HCID 90217539(4-Bromo-3-(difluoromethyl)phenyl)(ethyl)sulfaneYield 28.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-Bromo-2-(difluoromethyl)-4-fluorobenzene (Preparation 50, 772 mg, 3.43 mmol) and sodium ethanethiolate (352.7 mg, 3.77 mmol) in DMSO (5 mL) was heated at 50° C. for 18 hours. On cooling, water (70 mL) was added to the reaction mixture, the product was extracted with EtOAc (20 mL×3). The combined organic layers were concentrated to give the crude product, which was purified by silica gel column chromatography eluting with heptane to afford the title compound as a colourless oil (260 mg, 28%).

Workup

  1. temperatureOn cooling
  2. extractionthe product was extracted with EtOAc (20 mL×3)
  3. concentrationThe combined organic layers were concentrated
  4. customto give the crude product, which
  5. customwas purified by silica gel column chromatography
  6. washeluting with heptane

Sources & evidence

ORD record
ord-89e88194f2824ebc84ffce6e64c82f06
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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